5-halo-2-alkyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amines

ABSTRACT

This invention relates to novel triazolopyrimidines of the formula 
     
       
         
         
             
             
         
       
         
         
           
             in which R 1 , R 2 , R 3 , R 4 and X have the meanings given in the disclosure, to a plurality of processes for preparing these novel substances, and to their use for controlling unwanted microorganisms.
 
This invention further relates to novel intermediates of the formulae
 
           
         
       
    
     
       
         
         
             
             
         
       
     
                         
and processes for their preparation and additionally relates to novel amines and carbamates of the formulae given in the disclosure and processes for their preparation.

The present invention relates to novel triazolopyrimidines, to a plurality of processes for their preparation and to their use for controlling unwanted microorganisms. The invention furthermore relates to novel intermediates and to processes for their preparation.

It is already known that certain triazolopyrimidines have fungicidal properties (cf. EP-A 0 550 113, WO 94-20 501, EP-A 0 613-900, U.S. Pat. No. 5,612,345, EP-A 0 834 513, WO 98-46 607 and WO 98-46 608). The activity of these substances is good; however, at low application rates, it is sometimes unsatisfactory.

This invention, accordingly, provides novel triazolopyrimidines of the formula

in which

-   R¹ represents amino, hydroxyl, optionally substituted alkyl,     optionally substituted alkenyl, optionally substituted alkinyl,     optionally substituted cycloalkyl, optionally substituted alkoxy,     optionally substituted alkenyloxy, optionally substituted     alkinyloxy, optionally substituted cycloalkyloxy, optionally     substituted alkylamino, optionally substituted dialkylamino,     optionally substituted alkenylamino, optionally substituted     alkinylamino, optionally substituted cycloalkylamino, optionally     substituted N-cycloalkyl-N-alkylamino, optionally substituted     alkylideneamino, optionally substituted phenyl, optionally     substituted heterocyclyl or represents a radical of the formula     —S—R⁵, in which     -   R⁵ represents optionally substituted alkyl, optionally         substituted alkenyl, optionally substituted alkinyl or         optionally substituted cycloalkyl, -   R² represents hydrogen, optionally substituted alkyl, optionally     substituted alkenyl, optionally substituted alkinyl, or optionally     substituted cycloalkyl,     -   or -   R¹ and R² together with the nitrogen atom to which they are attached     represent an optionally substituted heterocyclic ring, -   R³ represents optionally mono- to tetrasubstituted aryl, -   R⁴ represents optionally substituted alkyl or represents optionally     substituted cycloalkyl and -   X represents halogen,     and also acid addition salts of those compounds of the formula (I)     in which -   R¹ represents amino.

Depending on substitution patterns, the compounds according to the invention may optionally be present as mixtures of different possible isomeric forms, particularly of stereoisomers, such as E and Z isomers, threo and erythro isomers, and optical isomers, for example, but also optionally of tautomers. If R³ is differently substituted on the two atoms adjacent to the bonding site, the compounds in question may be present in a particular form of stereoisomerism, namely as atropisomers.

Furthermore, it has been found that triazolopyrimidines of the formula (I) can be prepared by

-   a) reacting dihalogeno-triazolopyrimidines of the formula

-   -   in which     -   R³, R⁴ and X have the meanings given above and     -   Y¹ represents halogen     -   with amines of the formula

-   -   in which     -   R¹ and R² have the meanings given above,     -   if appropriate in the presence of a diluent and if appropriate         in the presence of an acid acceptor,     -   or

-   b) reacting triazolopyrimidines of the formula

-   -   in which     -   R², R³, R⁴ and X have the meanings given above     -   with sulphenyl halides of the formula         Y²—S—R⁵   (IV)     -   in which     -   R⁵ has the meanings given above and     -   Y² represents halogen,     -   if appropriate in the presence of a diluent and if appropriate         in the presence of an acid acceptor,     -   and, if appropriate, an acid is added onto the resulting         compounds of the formula (I) in which     -   R¹ represents amino.

Finally, it has been found that the novel triazolopyrimidines of the formula (I) and their acid addition salts are highly suitable for controlling unwanted microorganisms. In particular, they have strong fungicidal activity and can be used both in crop protection and in the protection of materials.

Surprisingly, the triazolopyrimidines of the formula (I) according to the invention have considerably better microbicidal activity than the constitutionally most similar prior-art substances of the same direction of action.

-   R¹ preferably represents hydroxyl, amino, represents alkyl having 1     to 6 carbon atoms which is optionally substituted by halogen, cyano,     hydroxyl, amino, phenyl, heterocyclyl, alkoxy having 1 to 4 carbon     atoms, alkoxycarbonyl having 1 to 4 carbon atoms, alkylamino having     1 to 4 carbon atoms, dialkylamino having 2 to 8 carbon atoms,     cycloalkyl having 3 to 6 carbon atoms, halogenocycloalkyl having 3     to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 4     carbon atoms, oxo, hydroxyimino and/or alkoxyimino having 1 to 4     carbon atoms,     -   represents alkenyl having 2 to 6 carbon atoms which is         optionally substituted by halogen, cycloalkyl, cyano, phenyl         and/or heterocyclyl,     -   represents alkinyl having 2 to 6 carbon atoms which is         optionally substituted by halogen, cycloalkyl, cyano, phenyl         and/or heterocyclyl,     -   represents cycloalkyl having 3 to 7 carbon atoms which is         optionally substituted by halogen, cycloalkyl, cyano,         halogenoalkyl having 1 to 2 carbon atoms and 1 to 5 halogen         atoms, phenyl and/or heterocyclyl,     -   represents alkoxy having 1 to 7 carbon atoms which is optionally         substituted by halogen, cycloalkyl, cyano, phenyl and/or         heterocyclyl,     -   represents alkenyloxy having 2 to 6 carbon atoms which is         optionally substituted by halogen, cycloalkyl, cyano, phenyl         and/or heterocyclyl,     -   represents alkinyloxy having 2 to 6 carbon atoms which is         optionally substituted by halogen, cycloalkyl, cyano, phenyl         and/or heterocyclyl,     -   represents cycloalkyloxy having 3 to 7 carbon atoms which is         optionally substituted by halogen, cycloalkyl, cyano, phenyl         and/or heterocyclyl,     -   represents alkylamino having 1 to 7 carbon atoms which is         optionally substituted by halogen, cycloalkyl, cyano, phenyl         and/or heterocyclyl,     -   represents dialkylamino having 1 to 7 carbon atoms in each of         the alkyl radicals which is optionally substituted by halogen,         cycloalkyl, cyano, phenyl and/or heterocyclyl,     -   represents alkenylamino having 2 to 6 carbon atoms which is         optionally substituted by halogen, cycloalkyl, cyano, phenyl         and/or heterocyclyl,     -   represents alkinylamino having 2 to 6 carbon atoms which is         optionally substituted by halogen, cycloalkyl, cyano, phenyl         and/or heterocyclyl,     -   represents optionally halogen-, cyano-, phenyl- and/or         heterocyclyl-substituted N-alkyl-N-alkenylamino having 1 to 6         carbon atoms in the alkyl moiety and 2 to 6 carbon atoms in the         alkenyl moiety,     -   represents cycloalkylamino having 3 to 7 carbon atoms which is         optionally substituted by halogen, cycloalkyl, cyano, phenyl         and/or heterocyclyl,     -   represents N-cycloalkyl-N-alkyl-amino having 3 to 7 carbon atoms         in the cycloalkyl moiety and 1 to 7 carbon atoms in the alkyl         moiety which is optionally substituted by halogen, cycloalkyl,         cyano, phenyl and/or heterocyclyl,     -   represents alkylideneamino having 2 to 6 carbon atoms which is         optionally substituted by halogen, cycloalkyl, cyano, phenyl         and/or heterocyclyl,     -   represents phenyl which is optionally substituted by halogen,         cycloalkyl, cyano, phenyl and/or heterocyclyl,     -   represents heterocyclyl having 5 or 6 ring members which is         optionally substituted by halogen, alkyl, cycloalkyl, cyano,         phenyl and/or heterocyclyl or     -   represents heterocyclyloxy having 5 or 6 ring members which is         optionally substituted by halogen, alkyl, cycloalkyl, cyano,         phenyl and/or heterocyclyl,     -   represents —SR⁵, in which     -   R⁵ represents alkyl having 1 to 6 carbon atoms which is         optionally substituted by halogen, cycloalkyl, cyano, phenyl         and/or heterocyclyl,         -   represents alkenyl having 2 to 6 carbon atoms which is             optionally substituted by halogen, cycloalkyl, cyano, phenyl             and/or heterocyclyl,         -   represents alkinyl having 2 to 6 carbon atoms which is             optionally substituted by halogen, cycloalkyl, cyano, phenyl             and/or heterocyclyl         -   or         -   represents cycloalkyl having 3 to 7 carbon atoms which is             optionally substituted by halogen, cycloalkyl, cyano, phenyl             and/or heterocyclyl,     -   where the heterocyclyl radicals mentioned above may be mono- to         trisubstituted by identical or different substituents from the         group consisting of         -   halogen, hydroxyl, phenyl, 1,2-dioxyethylene, alkyl having 1             to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms             and 1 to 5 halogen atoms, alkoxy having 1 to 4 carbon atoms,             alkylthio having         -   1 to 4 carbon atoms, halogenoalkoxy having 1 or 2 carbon             atoms and 1 to 5 halogen atoms, halogenoalkylthio having 1             or 2 carbon atoms and 1 to 5 halogen atoms, and where the             heterocyclyl radicals mentioned above are saturated or             partially unsaturated,     -   and where the phenyl radicals mentioned above may be mono- to         trisubstituted by identical or different substituents from the         group consisting of         -   halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl,             carbamoyl, thiocarbamoyl;         -   in each case straight-chain or branched alkyl, alkoxy,             alkylthio, alkylsulphinyl or alkylsulphonyl having in each             case 1 to 6 carbon atoms;         -   in each case straight-chain or branched alkenyl or             alkenyloxy having in each case 2 to 6 carbon atoms;         -   in each case straight-chain or branched halogenoalkyl,             halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or             halogenoalkylsulphonyl having in each case 1 to 6 carbon             atoms and 1 to 13 identical or different halogen atoms;         -   in each case straight-chain or branched halogenoalkenyl or             halogenoalkenyloxy having in each case 2 to 6 carbon atoms             and 1 to 13 identical or different halogen atoms;         -   in each case straight-chain or branched alkylamino,             dialkylamino, alkylcarbonyl, alkylcarbonyloxy,             alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl or             alkoximinoalkyl having in each case 1 to 6 carbon atoms in             the individual alkyl moieties;         -   cycloalkyl having 3 to 6 carbon atoms,         -   1,3-propanediyl, 1,4-butanediyl, methylenedioxy (—O—CH₂—O—)             or 1,2-ethylenedioxy (—O—CH₂—CH₂—O—) which is attached in             the 2,3-position, where these radicals may be mono- or             polysubstituted by identical or different substituents from             the group consisting of halogen, alkyl having 1 to 4 carbon             atoms and/or halogenoalkyl having 1 to 4 carbon atoms and 1             to 9 identical or different halogen atoms, -   R² preferably represents hydrogen,     -   represents alkyl having 1 to 4 carbon atoms which is optionally         substituted by halogen, cycloalkyl having 3 to 6 carbon atoms,         alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4         carbon atoms, oxo, hydroximino and/or alkoximino having 1 to 4         carbon atoms,     -   represents alkenyl having 2 to 4 carbon atoms which is         optionally substituted by halogen and/or cycloalkyl having 3 to         6 carbon atoms,     -   represents alkinyl having 2 to 4 carbon atoms which is         optionally substituted by halogen and/or cycloalkyl having 3 to         6 carbon atoms or     -   represents cycloalkyl having 3 to 6 carbon atoms which is         optionally substituted by halogen and/or cycloalkyl having 3 to         6 carbon atoms. -   R¹ and R² preferably represent, together with the nitrogen atom to     which they are attached, a 3- to 6-membered heterocyclic ring which     is saturated or partially saturated, which may in addition to the     nitrogen atom already mentioned contain a further heteroatom from     the series consisting of nitrogen, oxygen and sulphur, and which may     be substituted from one to three times by identical or different     substituents selected from halogen, hydroxyl, cyano, morpholinyl,     amino, a fused phenyl ring or a methylene or ethylene bridge,     -   alkyl having 1 to 4 carbon atoms,     -   halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or         different halogen atoms;     -   alkylcarbonylamino having 1 to 4 carbon atoms,     -   dialkylamino having 2 to 8 carbon atoms,     -   alkoxycarbonylamino having 1 to 4 carbon atoms,     -   di(alkoxycarbonyl)amino having 2 to 8 carbon atoms,     -   hydroxyalkyl having 1 to 4 carbon atoms,     -   alkoxycarbonyl having 1 to 4 carbon atoms and/or     -   alkylcarbonyl having 1 to 4 carbon atoms. -   R³ preferably represents phenyl which may be mono- to     tetrasubstituted by identical or different substituents from the     group consisting of     -   halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl,         carbamoyl, thiocarbamoyl;     -   in each case straight-chain or branched alkyl, alkoxy,         alkylthio, alkylsulphinyl or alkylsulphonyl having in each case         1 to 6 carbon atoms;     -   in each case straight-chain or branched alkenyl or alkenyloxy         having in each case 2 to 6 carbon atoms;     -   in each case straight-chain or branched halogenoalkyl,         halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or         halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms         and 1 to 13 identical or different halogen atoms;     -   in each case straight-chain or branched halogenoalkenyl or         halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1         to 11 identical or different halogen atoms;     -   in each case straight-chain or branched alkylamino,         dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl,         alkylsulphonyloxy, hydroximinoalkyl or alkoximinoalkyl having in         each case 1 to 6 carbon atoms in the individual alkyl moieties;     -   cycloalkyl having 3 to 6 carbon atoms,     -   1,3-propanediyl, 1,4-butanediyl, methylenedioxy (—O—CH₂—O—) or         1,2-ethylenedioxy (—O—CH₂—CH₂—O—) which is attached in the         2,3-position, where these radicals may be mono- or         polysubstituted by identical or different substituents from the         group consisting of halogen, alkyl having 1 to 4 carbon atoms         and/or halogenoalkyl having 1 to 4 carbon atoms and 1 to 9         identical or different halogen atoms. -   R⁴ preferably represents alkyl having 1 to 4 carbon atoms which is     optionally substituted by 1 to 9 halogen atoms or represents     cycloalkyl having 3 to 6 carbon atoms which is optionally     substituted by 1 to 9 halogen atoms. -   X preferably represents fluorine, chlorine or bromine. -   R¹ particularly preferably represents hydroxyl, amino, represents     methyl, ethyl, n-propyl, isopropyl, n-, iso-, s- or t-butyl,     methoxymethyl, 2-methoxyethyl, methylthiomethyl, 2-methylthioethyl,     hydroximinomethyl, methoximinomethyl, acetylmethyl,     2-hydroximinopropyl, 2-methoximinopropyl, allyl,     2-methylprop-2-enyl, propargyl, 2,2,2-trifluoroethyl,     1-(trifluoromethyl)ethyl, 3,3,3-trifluoropropyl, cyclopentyl,     cyclohexyl,     -   cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy,         difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,         trifluoroethoxy,     -   methylamino, ethylamino, n- or isopropylamino, n-, iso-, s- or         t-butylamino, dimethylamino, diethylamino, trifluoroethylamino,         cyclohexylmethylamino, 2-cyanoethylamino, allylamino,         1-cyclopropylethylamino, cyclopropylamino, cyclobutylamino,         cyclopentylamino, cyclohexylamino, 1-methylethylideneamino,         phenyl, benzyloxy, piperidinyl, morpholinyl, pyridylmethoxy,         thiazolylmethoxy, or represents —S—R⁵, in which     -   R⁵ represents methyl, ethyl, n- or isopropyl, difluoromethyl,         difluorochloromethyl, dichlorofluoromethyl or trifluoromethyl,     -   or -   R¹ represents (2,2-dichlorocyclopropyl)methyl, (2-furyl)methyl,     (2-tetrahydrofuryl)methyl, (2-tetrahydropyranyl)methyl,     1,2-dimethylpropyl, 1,3-dioxolan-2-ylmethyl, 1-cyclopropylethyl,     1-cyclopropylethylamino, 1-methylethylideneamino,     2,2,2-trifluoro-1-methylethyl, 2,4-dichlorobenzyloxy,     2,6-dichlorobenzyloxy, 2-butyl, 2-chlorobenzyloxy,     2-fluorocyclopropyl, 2-hexahydropyranyloxy, 2-methoxyethyl,     2-thienylmethyl, 2-tolyl, 2-trifluoromethylcyclohexyl,     3-(dimethylamino)propyl, 3,5-bis-trifluoromethylcyclohexyl,     3,5-dichlorobenzyloxy, 3-aminopropyl, 3-chlorobenzyloxy, 3-tolyl,     3-trifluoromethylbenzyloxy, 3-trifluoromethylcyclohexyl,     2-trifluoromethylcyclohexyl, 4-trifluoromethylcyclohexyl,     4-chlorobenzyloxy, 4-fluorobenzyloxy, 4-fluorophenyl, 4-tolyl,     4-trifluoromethylbenzyloxy, 4-trifluoromethylcyclohexyl, allyl,     allylamino, allyloxy, benzyloxy, —C(CH₃)₂—CF₃, —C(CH₃)₂—CH₂—COCH₃,     —C₂H₅, —CH(CH₂OH)—COOCH₃, —CH(CH₃)—C(CH₃)₃—, —CH(CH₃)—CH(O—CH₃)₂—,     —CH(CH₃)—CH═CH₂—, —CH(CH₃)—CH₂—CH(CH₃)₂—, —CH(CH₃)—CH₂—O—CH₃—,     —CH(CH₃)—CH₂—OH, —CH(CH₃)—COOCH₃, —CH(CH₃)—COO-t-butyl,     —CH₂—C(CH₃)═CH₂, —CH₂—C(CH₃)₃, —CH₂—CF₃, —CH₂—CH(OCH₃)₂,     —CH₂—CH₂—CF₃, —CH₂—CH₂—Cl, —CH₂—CH₂—CN, —CH₂—CH₂—N(CH₃)₂,     —CH₂—CH₂—N(CH₃)₂, —CH₂—NH₂, —CH₂—CHF₂, —CH₂—CN, —CH₂—COOC₂H₅,     —CH₂—COOC₂H₅, —CH₂—COOCH₃, —CH₃, cyclohexyl, cyclopentyl,     cyclopropyl, cyclopropylmethyl, dimethylamino, isobutoxy, isobutyl,     isopropylamino, n-butoxy, n-butyl, n-butylamino, —NH₂,     —NH—CH₂—CF₂—CHF₂, —NH—CH₂—CF₃, —NH—CH₂—CH(CH₃)₂, —O—C₂H₅,     —O—CH(CH₃)—CH₂—CH₃, —O—CH₃, —OH, O-isopropyl, propargyl, t-butoxy,     t-butyl, t-butylamino, or represents a group

-   -   where the aforementioned thiazolyl and pyridyl radicals may be         mono- or disubstituted in the case of thiazolyl and mono- to         trisubstituted in the case of pyridyl, in each case by identical         or different fluorine, chlorine, bromine, methyl, ethyl, n- or         isopropyl, n-, iso-, s- or t-butyl, methoxy, ethoxy, n- or         isopropoxy, n-, iso-, s- or t-butoxy, methylthio, ethylthio, n-         or isopropylthio, difluoromethoxy, trifluoromethoxy,         difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,         difluorochloromethylthio, dichlorofluoromethylthio,         trifluoromethylthio and/or phenyl,     -   and where the aforementioned phenyl and benzyloxy radicals may         be substituted from one to three times in the phenyl moiety by         identical or different substituents selected from     -   fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl,         formyl, carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or         isopropyl, n-, iso-, s- or t-butyl, methoxy, ethoxy, n- or         isopropoxy, methylthio, ethylthio, n- or isopropylthio,         methylsulphinyl, ethylsulphinyl, methylsulphonyl or         ethylsulphonyl, trifluoromethyl, trifluoroethyl,         difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,         trifluoroethoxy, difluoromethylthio, difluorochloromethylthio,         trifluoromethylthio, trifluoromethylsulphinyl,         trifluoromethylsulphonyl, methylamino, ethylamino, n- or         isopropylamino, dimethylamino, diethylamino, acetyl, propionyl,         acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy,         ethylsulphonyloxy, hydroximinomethyl, hydroximinomethyl,         methoximinomethyl, ethoximinomethyl, methoximinoethyl,         ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopentyl or         cyclohexyl,     -   1,3-propanediyl, methylenedioxy (—O—CH₂—O—), 1,2-ethylenedioxy         (—O—CH₂—CH₂—O—) which is attached in the 2,3-position, where         these radicals may be mono- or polysubstituted by identical or         different substituents from the group comprising fluorine,         chlorine, methyl, ethyl, n-propyl, isopropyl and/or         trifluoromethyl.

-   R² particularly preferably represents hydrogen, methyl, ethyl, n- or     isopropyl, n-, iso-, s- or t-butyl, methoxymethyl, 2-methoxyethyl,     methylthiomethyl, 2-methylthioethyl, hydroximinomethyl,     methoximinomethyl, acetylmethyl, 2-hydroxyiminopropyl,     2-methoxyiminopropyl, allyl, propargyl, 2,2,2-trifluoroethyl,     1-(1,1,1-trifluoromethyl)ethyl, cyclopropylmethyl, cyclobutylmethyl,     cyclopentylmethyl or cyclohexylmethyl.

-   R¹ and R² particularly preferably represent, together with the     nitrogen atom to which they are attached, 1-pyrrolinyl,     3-pyrrolinyl, pyrrolidinyl, dihydropyridinyl, piperidinyl,     pyrazolinyl, pyrazolidinyl, imidazolinyl, imidiazolidinyl,     1,2-diazinanyl, 1,3-diazinanyl, piperazinyl, oxazolinyl,     oxazolidinyl, isoxazolyl, isoxazolidinyl, dihydrooxazinyl,     morpholinyl, thiazolinyl, thiazolidinyl, thiomorpholinyl, the said     heterocycles possibly being substituted by     -   fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl,         formyl, carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or         isopropyl, n-, iso-, s- or t-butyl, methoxy, ethoxy, n- or         isopropoxy, methylthio, ethylthio, n- or isopropylthio,         methylsulphinyl, ethylsulphinyl, methylsulphonyl or         ethylsulphonyl, trifluoromethyl, trifluoroethyl,         difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,         trifluoroethoxy, difluoromethylthio, difluorochloromethylthio,         trifluoromethylthio, trifluoromethylsulphinyl,         trifluoromethylsulphonyl, methylamino, ethylamino, n- or         isopropylamino, dimethylamino, diethylamino, acetyl, propionyl,         acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy,         ethylsulphonyloxy, hydroximinomethyl, hydroximinomethyl,         methoximinomethyl, ethoximinomethyl, methoximinoethyl,         ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopentyl or         cyclohexyl, by a fused phenyl ring or by a methanediyl or         ethanediyl bridge.

-   R³ particularly preferably represents phenyl which may be mono- to     trisubstituted by identical or different substituents from the group     consisting of     -   fluorine, chlorine, bromine, cyano, nitro, formyl, methyl,         ethyl, n- or isopropyl, n-, iso-, s- or t-butyl, allyl,         propargyl, methoxy, ethoxy, n- or isopropoxy, methylthio,         ethylthio, n- or isopropylthio, methylsulphinyl, ethylsulphinyl,         methylsulphonyl, ethylsulphonyl, allyloxy, propargyloxy,         trifluoromethyl, trifluoroethyl, difluoromethoxy,         trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy,         difluoromethylthio, difluorochloromethylthio,         trifluoromethylthio, trifluoromethylsulphinyl,         trifluoromethylsulphonyl, trichloroethinyloxy,         trifluoroethinyloxy, chloroallyloxy, iodopropargyloxy,         methylamino, ethylamino, n- or iso-propylamino, dimethylamino,         diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl,         ethoxycarbonyl, hydroximinomethyl, hydroximinoethyl,         methoximinomethyl, ethoximinomethyl, methoximinoethyl,         ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopentyl and         cyclohexyl,     -   1,3-propanediyl, methylenedioxy (—O—CH₂—O—) or 1,2-ethylenedioxy         (—O—CH₂—CH₂—O—) which is attached in the 2,3-position, where         these radicals may be mono- or polysubstituted by identical or         different substituents from the group consisting of fluorine,         chlorine, methyl, ethyl, n-propyl, isopropyl and         trifluoromethyl.

-   R⁴ particularly preferably represents methyl, ethyl, n-propyl,     isopropyl, n-, iso-, s- or t-butyl, trifluoromethyl, trifluoroethyl     or cyclopropyl.

-   X particularly preferably represents fluorine or chlorine.

-   R¹ and R² very particularly preferably together represent one of the     following groups:     -   —CH(CF₃)—CH₂—CH₂—CH₂—, —CH(CF₃)—CH₂—CH₂—CH₂—CH₂—,         —CH(CH₃)—CH═CH—CH(CH₃)—, —CH(CH₃)—CH₂—CH₂—O—, —CH(COOCH₃)—,         —CH₂—CH(CH₃)—CH₂—CH(CH₃)—CH₂—, —CH₂—CH(CH₃)—O—CH(CH₃)—CH₂—,         —CH₂—CH(NH₂)—CH₂—CH₂—CH₂—C—CH₂—CH(OH)—CH₂—CH₂—,         —CH₂—CH(OH)—CH₂—CH₂—CH₂— —CH₂—CH═C(C₂H₅)—CH₂—CH₂—,         —CH₂—CH₂—C(CH₃)₂—CH₂—CH₂— —CH₂—CH₂—CH₂—,         —CH₂—CH₂—CH(CF₃)—CH₂—CH₂— —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—,         —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— —CH₂—CH₂—CH(COCH₃)—CH₂—CH₂—,         —CH₂—CH₂—CH(COOCH₃)—CH₂—CH₂— —CH₂—CH₂—CH(NH—COCH₃)—CH₂—CH₂—,         —CH₂—CH₂—CH(OH)—CH₂—CH₂— —CH₂—CH₂—CH═C(CH₃)—CH₂—,         —CH₂—CH₂—CH═CH—CH₂— —CH₂—CH₂—CH₂—CH(CH₃)—,         —CH₂—CH₂—CH₂—CH(CH₃)—CH₂— —CH₂—CH₂—CH₂—CH₂—,         —CH₂—CH₂—CH₂—CH₂—CH(CH₃)— —CH₂—CH₂—CH₂—CH₂—CH₂—,         —CH₂—CH₂CHBr—CH₂—CH₂— —CH₂—CH₂—CHF—CH₂—CH₂—,         —CH₂—CH₂—N(CH₃)—CH₂—CH₂— —CH₂—CH₂—O—CH₂CH₂—, —CH₂—CH₂—S—CH₂—CH₂—         —CH₂—S—CH₂—CH₂—, —NH—CH₂—CH₂—CH₂—CH₂— —O—CH₂—CH₂CH(CH₃)—,         —O—CH₂—CH₂—CH₂—CH₂—,     -   or represent one of the following groups in which X₂ represents         the nitrogen atom to which the radicals R¹, R² are attached:

-   R² very particularly preferably represents hydrogen, methyl, ethyl,     n-, isopropyl, n-, iso-, s- or t-butyl. -   R³ very particularly preferably represents phenyl which is mono- to     trisubstituted by identical or different fluorine and/or chlorine     substituents in positions 2, 4 and 6: -   X very particularly preferably represents chlorine.

Very particular preference is further given to those compounds of the formula (I) in which

-   R¹, R², R⁴ and X have the preferred definitions stated above and -   R³ represents 2,4-disubstituted, 2,6-disubstituted or     2,4,6-trisubstituted phenyl.

Very particular preference is further given to those compounds of the formula (I) in which

-   R¹, R², R⁴ and X have the aforementioned definitions and -   R³ represents 2-chloro-4-fluorophenyl, 2-chloro-6-fluorophenyl or     2-chloro-4,6-difluorophenyl.

Very particular preference is further given to those compounds of the formula (I) in which

-   R¹, R², R³ and X have the aforementioned definitions and -   R⁴ represents cyclopropyl.

Very particular preference is further given to those compounds of the formula (I) in, which

-   X, R³, and R⁴ have the aforementioned definitions and -   R¹ represents hydrogen and -   R² represents —CH(CH₃)CF₃.

Another very particularly preferred group of compounds are those triazolopyrimidines of the formula (I), in which

-   R⁴ represents cyclopropyl and -   R¹, R², R³ and X have the definitions stated before as being     preferred.

The radical definitions mentioned above can be combined with one another as desired. Moreover, individual meanings may not apply.

Preferred compounds according to the invention are also adducts of acids and those triazolopyrimidines of the formula (I), in which

-   R¹ represents amino and -   R², R³, R⁴ and X have those definitions which were stated as being     preferred for these radicals.

The acids which can be used for addition reaction include preferably hydrohalic acids, such as hydrochloric and hydrobromic acid, for example, especially hydrochloric acid, and also phosphoric acid, nitric acid, monofunctional and difunctional carboxylic acids and hydroxycarboxylic acids, such as acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid and lactic acid, for example, and sulphonic acids, such as p-toluenesulphonic acid, 1,5-naphthalenedisulphonic acid, saccharin and thiosaccharin.

Using 5,7-dichloro-2-(trifluoromethyl)-6-(2,4,6-trifluorophenyl)-[1,2,4]-triazolo[1,5-a]-pyrimidine and 4-trifluoromethylpiperidine as starting materials, the course of the process (a) according to the invention can be illustrated by the formula scheme below.

Using 5-chloro-2-(trifluoromethyl)-N-[(1S)-2,2,2-trifluoro-1-methyl-ethyl]-6-(2,4,6-trifluorophenyl)-[1,2,4]-triazolo-[1,5-a]pyrimidin-7-amine and dichlorofluoromethane-sulphenyl chloride as starting materials, the course of the process (b) according to the invention, can be illustrated by the formula scheme below.

The formula (II) provides a general definition of the dihalogeno-triazolo-pyrimidines required as starting materials for carrying out the process (a) according to the invention. In this formula, R³, R⁴ and X preferably have those meanings which have already been mentioned in connection with the description of the substances of the formula (I) according to the invention as being preferred for these radicals. Y¹ preferably represents fluorine, chlorine or bromine, particularly preferably fluorine or chlorine.

The dihalogeno-triazolopyrimidines of the formula (II) are novel. These substances, too, are suitable for controlling unwanted microorganisms.

The dihalogeno-triazolopyrimidines can be prepared by

-   c) reacting dihydroxy-triazolo-pyrimidines of the formula

-   -   in which     -   R³ and R⁴ have the meanings given above,     -   with halogenating agents, if appropriate in the presence of a         diluent.

The formula (V) provides a general definition of the dihydroxy-triazolopyrimidines required as starting materials for carrying out the process (c). In this formula, R³ and R⁴ preferably have those meanings which have already been mentioned in connection with the description of the substances of the formula (I) according to the invention as being preferred for these radicals.

The dihydroxytriazolopyrimidines of the formula (V), too, have hitherto not been known. They can be prepared by

-   d) reacting arylmalonic esters of the formula

-   -   in which     -   R³ has the meanings given above and     -   R⁶ represents alkyl having 1 to 4 carbon atoms     -   with aminotriazoles of the formula

-   -   in which     -   R⁴ has the meanings given above,     -   if appropriate in the presence of a diluent and if appropriate         in the presence of an acid binder.

The formula (VI) provides a general definition of the arylmalonic esters required as starting materials for carrying out the process (d). In this formula, R³ preferably has those meanings which have already been mentioned in connection with the description of the substances of the formula (I) according to the invention as being preferred for this radical. R⁶ preferably represents methyl or ethyl.

The arylmalonic esters of the formula (VI) are known or can be prepared by known methods (cf. U.S. Pat. No. 6,156,925).

The formula (VII) provides a general definition of the aminotriazoles furthermore required as starting materials for carrying out the process (d). In this formula, R⁴ preferably has those meanings which have already been mentioned in connection with the description of the substances of the formula (I) according to the invention as being preferred for this radical.

The aminotriazoles of the formula (VII) are known or can be prepared by known methods (cf. J. Org. Chem. (1974), 39(11) 1522–1526, Khim. Geterotsikl. Soedin. (1989), (2) 278, or Zh. Obshch. Khim. (1969), 39(11)) 2525–2528.

Suitable diluents for carrying out the process (d) are all inert organic solvents which are customary for such reactions. Preference is given to using alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol.

Suitable acid binders for carrying out the process (d) are all inorganic and organic bases which are customary for such reactions. Preference is given to using tertiary amines, such as tributylamine or pyridine. Amine used in excess may also act as diluent.

When carrying the process (d), the temperatures may be varied within a relatively wide range. In general, the process is carried out at temperatures between 20° C. and 200° C., preferably between 50° C. and 180° C.

The process (d) is generally carried out under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure.

When carrying out the process (d), arylmalonic esters of the formula (VI) and aminotriazole of the formula (VII) are generally employed in equivalent amounts. However, it is also possible to use an excess of one or the other component. Work-up is carried out by-customary methods.

Suitable halogenating agents for carrying out the process (d) are all components which are customarily used for replacing hydroxyl groups by halogen. Preference is given to using phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, phosphorus oxychloride, thionyl chloride, thionyl bromide or mixtures thereof. The corresponding fluoro compounds of the formula (II) can be prepared from the chloro or bromo compounds by reaction with potassium fluoride.

Suitable diluents for carrying out the process (c) are all solvents which are customary for such halogenations. Preference is given to using halogenated aliphatic or aromatic hydrocarbons, such as chlorobenzene. However, it is also possible for the halogenating agent itself, for example phosphorus oxychloride or a mixture of halogenating agents, to act as diluent.

When carrying out the process (c), too, the temperatures can be varied within a relatively wide range. In general, the process is carried out at temperatures between 0° C. and 150° C., preferably between 10° C. and 120° C.

The process (c) is generally carried out under atmospheric pressure. However, it is also possible to operate under elevated pressure.

When carrying out the process (d), the dihydroxy-triazolopyrimidine of the formula (V) is generally reacted with an excess of halogenating agent. Work-up is carried out by customary methods.

The formula (III) provides a general definition of the amines furthermore required as starting materials for carrying out the process (a) according to the invention. In this formula, R¹ and R² preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred for R¹ and R².

Some of the amines of the formula (III) are known.

Novel amines are those of the formula (IIIa),

in which

-   R⁷ represents isobutyl, 2-methoxyethyl or represents

The amines of the formula (IIIa) may be prepared by

-   e) in a first stage reacting ethyl N-methoxycarbamide of the formula     (VIII)

-   -   with halogen compounds of the formula (IX),         R⁷—X¹   (IX)     -   in which     -   R⁷ has the meanings given above and     -   X¹ represents bromine or iodine     -   in the presence of a base and in the presence of a diluent and         in a second stage reacting the resulting carbamates of the         formula (X)

-   -   in which     -   R⁷ has the meanings given above     -   with potassium hydroxide in the presence of ethanol and water.     -   Also novel are amines of the formula (IIIb)

-   -   in which     -   R⁷ has the meanings given above.

The amines of the formula (IIIb) may be prepared by

-   f) in a first stage reacting ethyl N-hydroxy-N-methylcarbamate of     the formula (XI)

-   -   with halogen compounds of the formula (IX),         R⁷—X¹   (IX)     -   in which     -   R⁷ and X¹ have the meanings given above     -   in the presence of a base and in the presence of a diluent and         in a second stage reacting the resulting carbamates of the         formula (XII),

-   -   in which     -   R⁷ has the meanings given above     -   with potassium hydroxide in the presence of ethanol and water.     -   Also novel are trifluoroisopropylamines of the formula (IIIc)

-   -   in which     -   R⁸ represents methyl, ethyl or propyl.

The trifluoroisopropylamines of the formula (IIIc) may be prepared by

-   g) in a first stage reacting ethyl N-trifluoroisopropylcarbamate of     the formula (XIII),

-   -   with halogen compounds of the formula (XIV),         R⁸—X¹   (XIV)     -   in which     -   R⁸ and X¹ have the meanings given above     -   in the presence of a base and in the presence of a diluent and         in a second stage reacting the resulting carbamates of the         formula (XV)

-   -   in which     -   R⁸ has the meanings given above     -   with potassium hydroxide in the presence of ethanol and water.

Also novel, finally, is the 3-trifluoromethyl-3-aminopropene of the formula (III-4)

The 3-trifluoromethyl-3-aminopropene of the formula (IIId) may be prepared by

-   h) reacting the carbamate of the formula (XVI)

-   -   with aqueous hydrochloric acid.

The compounds of the formulae (VIII), (IX), (XI), (XIII), (XIV) and (XVI) required as starting materials when carrying out the processes (e)–(g) according to the invention are known or may be prepared by known methods.

Suitable organic and inorganic acid acceptors for carrying out the first stage of the processes (e), (f) and (g) according to the invention include in each case all those which are customary for such reactions.

With preference it is possible to use alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate and sodium carbonate, and also ammonium compounds, such as ammonium hydroxide, ammonium acetate and ammonium carbonate. As organic bases mention may be made of the following: tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

As diluents when carrying out the first stage of the processes (e), (f) and (g) according to the invention, suitable compounds, include in each case all customary inert organic solvents. With preference it is possible to use ethers, such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide or N-methylpyrrolidone; sulphones, such as sulpholane, alcohols such as methanol, ethanol, isopropanol, tert-butanol, n-butanol.

The reaction temperatures when carrying out the first stage of the processes, (e), (f) and (g) according to the invention may in each case be varied within a relatively wide range. It is normal to operate at temperatures between 0° C. and 150° C., preferably between 10° C. and 100° C.

When carrying out the first stage of the processes (e), (f) and (g) according to the invention it is normal to operate in each case under atmospheric pressure. It is, however, also possible to operate under increased pressure or, where no low-boiling components participate in the reaction, under reduced pressure.

When carrying out the first stage of the processes (e), (f) and (g) according to the invention

-   -   generally from 0.5 to 15 mol, preferably from 1 to 5 mol, of         halogen compound of the formula (IX) are used per mole of ethyl         N-methoxycarbamate of the formula (VIII), or     -   generally from 0.5 to 15 mol, preferably from 1 to 5 mol, of         halogen compound of the formula (IX) are used per mole of ethyl         N-hydroxy-N-methylcarbamate of the formula (XI) or     -   generally from 0.5 to 15 mol, preferably from 1 to 5 mol, of         halogen compound of the formula (XIV) are used per mole of ethyl         N-trifluoroisopropylcarbamate of the formula (XII).

Working up takes place in each case in accordance with customary methods, for example by extraction and subsequent drying or by precipitation with subsequent filtration and drying. Any impurities still present may be removed by customary methods.

The compounds of the formulae (X), (XII) and (XV) obtained as intermediates when carrying out the first stage of the processes (e), (f) and (g) according to the invention are novel.

When carrying out the second stage of the processes (e), (f) and (g) according to the invention as well it is possible to vary the reaction temperatures in each case within a relatively wide range. It is normal to operate at temperatures between 0° C. and 100° C., preferably between 10° C. and 80° C.

When carrying out the second stage of the processes (e), (f) and (g) according to the invention as well it is normal to operate in each case under atmospheric pressure. It is, however, again possible to operate in each case under increased pressure or, where the products to be isolated do not have very low boiling points, to operate under reduced pressure.

When carrying out the second stage of the processes (e), (f) and (g) according to the invention in each case up to 10 mol of potassium hydroxide are used per mole of a compound of the formula (X), (XII) or (XV). Working up takes place in accordance with customary methods. The amines are appropriately isolated in the form of their salts, generally by addition of acid, preferably aqueous hydrochloric acid.

When carrying out the process (h) of the invention it is likewise possible to vary the reaction temperatures within a relatively wide range. It is normal to operate at temperatures between 10° C. and 150° C., preferably at reflux temperature.

It is normal when carrying out the process (h) according to the invention to operate under atmospheric pressure. It is, however, also possible to operate under increased pressure.

When carrying out the process (h) according to the invention an excess, preferably up to 10 mol, of aqueous hydrochloric acid is used per mole of carbamate of the formula (XVI). Working up takes place again in accordance with customary methods.

The formula (Ia) provides a general definition of the triazolopyrimidines required as starting materials for carrying out the process (b) according to the invention. In this formula, R², R³, R⁴ and X preferably have those meanings which have already been mentioned in connection with the description of the substances of the formula (I) according to the invention as being preferred for these radicals.

The triazolopyrimidines of the formula (Ia) are substances according to the invention. They can be prepared by process (a) according to the invention.

The formula (IV) provides a general definition of the sulphenyl halides furthermore required as starting materials for carrying out the process (b) according to the invention. In this formula, R⁵ preferably has those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred for this radical.

Y² preferably represents fluorine, chlorine or bromine, particularly preferably chlorine.

The sulphenyl halides of the formula (IV) are known or can be prepared by known methods.

Suitable diluents for carrying out the process (a) according to the invention are all customary inert organic solvents. Preference is given to using aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane or 1,2-diethoxyethane; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidone; esters, such as methyl acetate or ethyl acetate; sulphoxides; such as dimethyl sulphoxide; sulphones, such as sulpholane.

Suitable acid acceptors for carrying out the process (a) according to the invention are all acid binders which are customary for such reactions. Preference is given to using tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

When carrying out the process (a) according to the invention, the reaction temperatures may be varied within a relatively wide range. In general, the process is carried out at temperatures between 0° C. and 150° C., preferably at temperatures between 0° C. and 80° C.

Both the process (a) and the process (b) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure, in general between 0.1 and 10 bar.

When carrying out the process (a) according to the invention, in general from 0.5 to 10 mol, preferably from 0.8 to 2 mol, of the amine of the formula (III) are employed per mole of dihalogeno-triazolo-pyrimidine of the formula (II). Work-up is carried out by customary methods.

For the preparation of acid addition salts of triazolopyrimidines of the formula (I), suitable acids, preferably include those already mentioned as preferred acids in connection with the description of the acid addition salts according to the invention.

The acid addition salts of the compounds of the formula (I) may be obtained in a simple way in accordance with customary salt formation methods, e.g. by dissolving a compound of the formula (I) in a suitable inert solvent and adding the acid, e.g. hydrochloric acid, and isolating the salt in a known way, by filtration, for example, and purifying it if appropriate by washing with an inert organic solvent.

The substances according to the invention have potent microbicidal activity and can be employed for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.

Fungicides can be employed in crop protection for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be employed in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come under the generic names listed above may be mentioned as examples, but not by way of limitation:

-   Xanthomonas species, such as, for example, Xanthomonas campestris     pv. oryzae; -   Pseudomonas species, such as, for example, Pseudomonas syringae pv.     lachrymans; -   Erwinia species, such as, for example, Erwinia amylovora; -   Pythium species, such as, for example, Pythium ultimum; -   Phytophthora species, such as, for example, Phytophthora infestans; -   Pseudoperonospora species, such as, for example, Pseudoperonospora     humuli or Pseudoperonospora cubensis; -   Plasmopara species, such as, for example, Plasmopara viticola; -   Bremia species, such as, for example, Bremia lactucae; -   Peronospora species, such as, for example, Peronospora pisi or P.     brassicae; -   Erysiphe species, such as, for example, Erysiphe graminis; -   Sphaerotheca species, such as, for example, Sphaerotheca fuliginea; -   Podosphaera species, such as, for example, Podosphaera leucotricha; -   Venturia species, such as, for example, Venturia inaequalis; -   Pyrenophora species, such as, for example, Pyrenophora teres or P.     graminea (conidia form: Drechslera, syn: Helminthosporium); -   Cochliobolus species, such as, for example, Cochliobolus sativus     (conidia form: Drechslera, syn: Helminthosporium); -   Uromyces species, such as, for example, Uromyces appendiculatus; -   Puccinia species, such as, for example, Puccinia recondita; -   Sclerotinia species, such as, for example, Sclerotinia sclerotiorum; -   Tilletia species, such as, for example, Tilletia caries; -   Ustilago species, such as, for example, Ustilago nuda or Ustilago     avenae; -   Pellicularia species, such as, for example, Pellicularia sasakii; -   Pyricularia species, such as, for example, Pyricularia oryzae; -   Fusarium species, such as, for example, Fusarium culmorum; -   Botrytis species, such as, for example, Botrytis cinerea; -   Septoria species, such as, for example, Septoria nodorum; -   Leptosphaeria species, such as, for example, Leptosphaeria nodorum; -   Cercospora species, such as, for example, Cercospora canescens; -   Alternaria species, such as, for example, Alternaria brassicae; and

Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.

The active compounds according to the invention also have very good fortifying action in plants. Accordingly, they can be used for mobilizing the defences of the plant against attack by unwanted microorganisms.

In the present context, plant-fortifying (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defence system of plants such that, when the treated plants are subsequently inoculated with unwanted microorganisms, they show substantial resistance against these microorganisms.

In the present case, unwanted microorganisms are to be understood as meaning phytopathogenic fungi, bacteria and viruses. Accordingly, the substances according to the invention can be used to protect plants for a certain period after the treatment against attack by the pathogens mentioned. The period for which protection is provided generally extends over 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active compounds.

The fact that the active compounds are well tolerated by plants at the concentrations required for controlling plant diseases permits the treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.

The active compounds according to the invention are also suitable for increasing the yield of crops. In addition, they show reduced toxicity and are well tolerated by plants.

At certain concentrations and application rates, the active compounds according to the invention can also be used as herbicides, for influencing plant growth and for controlling animal pests. They can also be used as intermediates and precursors for the synthesis of further active compounds.

The active compounds according to the invention can be used to treat all plants and parts of plants. By plants are understood here all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or cannot be protected by varietal property rights. Parts of plants are to be understood as meaning all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubers and rhizomes. Parts of plants also include harvested plants and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of the plants and the parts of plants with the active compounds according to the invention is carried out directly or by action on their surroundings, habitat or storage space, according to customary treatment methods, for example by dipping, spraying, evaporating, atomizing, broadcasting, spreading-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multi-layer coating.

In the protection of materials, the compounds according to the invention can be employed for protecting industrial materials against infection with, and destruction by, undesired microorganisms.

Industrial materials in the present context are understood as meaning non-living materials which have been prepared for use in industry. For example, industrial materials which are intended to be protected by active compounds according to the invention from microbial change or destruction can be adhesives, sizes, paper and board, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be infected with, or destroyed by, microorganisms. Parts of production plants, for example cooling-water circuits, which may be impaired by the proliferation of microorganisms may also be mentioned within the scope of the materials to be protected. Industrial materials which may be mentioned within the scope of the present invention are preferably adhesives, sizes, paper and board, leather, wood, paints, cooling lubricants and heat-transfer liquids particularly preferably wood.

Microorganisms capable of degrading or changing the industrial materials which may be mentioned are, for example, bacteria, fungi, yeasts, algae and slime organisms. The active compounds according to the invention preferably act against fungi, in particular moulds, wood-discolouring and wood-destroying fungi (Basidiomycetes), and against slime organisms and algae.

Microorganisms of the following genera may be mentioned as examples:

-   Alternaria, such as Alternaria tenuis, -   Aspergillus, such as Aspergillus niger, -   Chaetomium, such as Chaetomium globosum, -   Coniophora, such as Coniophora puetana, -   Lentinus, such as Lentinus tigrinus, -   Penicillium, such as Penicillium glaucum, -   Polyporus, such as Polyporus versicolor, -   Aureobasidium, such as Aureobasidium pullulans, -   Sclerophoma, such as Sclerophoma pityophila, -   Trichoderma, such as Trichoderma viride, -   Escherichia, such as Escherichia coli, -   Pseudomonas, such as Pseudomonas aeruginosa, and -   Staphylococcus, such as Staphylococcus aureus.

Depending on their particular physical and/or chemical properties, the active compounds can be converted to the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is, liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers. If the extender used is water, it is also possible to employ, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide or dimethyl sulphoxide, or else water. Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at standard temperature and under atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons, or else butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: for example ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates. Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks. Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates. Suitable dispersants are for example lignosulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations, also in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, to broaden, for example, the activity spectrum or to prevent development of resistance. In many cases, synergistic effects are obtained, i.e. the activity of the mixture is greater than the activity of the individual components.

Examples of Suitable Mixing Components are the Following:

Fungicides:

-   aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine,     azaconazole, azoxystrobin, -   benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl,     bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,     bromuconazole, bupirimate, buthiobate, -   calcium polysulphide, capsimycin, captafol, captan, carbendazim,     carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,     chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,     cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,     carpropamide, -   debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,     dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,     diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,     ditalimfos, dithianon, dodemorph, dodine, drazoxolon, -   edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole, -   famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram,     fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate,     fentin hydroxide, ferbam, ferimzone, fluazinam, flumetover,     fluoromide, fluquinconazole, flurprimidol, flusilazole,     flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium,     fosetyl-sodium, fthalide, fuberidazole, furalaxyl, furametpyr,     furcarbonil, furconazole, furconazole-cis, furmecyclox, fenhexamide, -   guazatine, -   hexachlorobenzene, hexaconazole, hymexazole, -   imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,     iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),     iprodione, irumamycin, isoprothiolane, isovaledione, iprovalicarb -   kasugamycin, kresoxim-methyl, copper preparations, such as: copper     hydroxide, copper naphthenate, copper oxychloride, copper sulphate,     copper oxide, oxine-copper and Bordeaux mixture, -   mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,     metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,     metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin, -   nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol, -   ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim,     oxyfenthiin, -   paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,     picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim,     probenazole, prochloraz, procymidone, propamocarb,     propanosine-sodium, propiconazole, propineb, pyraclostrobin,     pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur, -   quinconazole, quintozene (PCNB), quinoxyfen, -   sulphur and sulphur preparations, spiroxamines, -   tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole,     thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,     tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,     triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,     trifloxystrobin, triflumizole, triforine, triticonazole, -   uniconazole, -   validamycin A, vinclozolin, viniconazole, -   zarilamide, zineb, ziram and also -   Dagger G, -   OK-8705, -   OK-8801, -   α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol, -   α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol, -   α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol, -   α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol, -   (5RS,     6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone, -   (E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide, -   1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone     O-(phenylmethyl)-oxime, -   1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione, -   1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione, -   1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene, -   1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole, -   1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole, -   1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole, -   1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole, -   2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide, -   2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate, -   2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide, -   2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide, -   2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole, -   2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole, -   2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile, -   2-aminobutane, -   2-bromo-2-(bromomethyl)-pentanedinitrile, -   2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide, -   2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide, -   2-phenylphenol (OPP), -   3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrole-2,5-dione, -   3,5-dichloro-N-[cyano[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide, -   3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile, -   3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine, -   4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide, -   4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one, -   8-hydroxyquinoline sulphate, -   9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide, -   bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate, -   cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol, -   cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholine-hydrochloride, -   ethyl [(4-chlorophenyl)-azo]-cyanoacetate, -   potassium hydrogen carbonate, -   methanetetrathiol sodium salt, -   methyl     1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate, -   methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate, -   methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate, -   N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide, -   N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide, -   N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide, -   N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine, -   N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine, -   N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide, -   N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide, -   N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide, -   N-[3-chloro-4,5-bis-(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide, -   N-formyl-N-hydroxy-DL-alanine-sodium salt, -   O,O-diethyl     [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate, -   O-methyl S-phenyl phenylpropylphosphoramidothioate, -   S-methyl 1,2,3-benzothiadiazole-7-carbothioate, -   spiro[2H]-1-benzopyrane-2,1′(3′H)-isobenzofuran]-3′-one, -   4-[(3,4-dimethoxyphenyl)-3-(4-fluorophenyl)-acryloyl]-morpholine.     Bactericides: -   bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,     kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,     probenazole, streptomycin, tecloftalam, copper sulphate and other     copper preparations.     Insecticides/Acaricides/Nematicides: -   abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,     aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz, avermectin,     AZ 60541, azadirachtin, azamethiphos, azinphos A, azinphos M,     azocyclotin, -   Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus     thuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella,     bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,     bifenazate, bifenthrin, bioethanomethrin, biopermethrin,     bistrifluron, BPMC, bromophos A, bufencarb, buprofezin, butathiofos,     butocarboxim, butylpyridaben, -   cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan,     cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,     chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,     chlovaporthrin, chromafenozide, cis-resmethrin, cispermethrin,     clocythrin, cloethocarb, clofentezine, clothianidine, cyanophos,     cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin,     cypermethrin, cyromazine, -   deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,     diazinon, dichlorvos, dicofol, diflubenzuron, dimethoat,     dimethylvinphos, diofenolan, disulfoton, docusat-sodium, dofenapyn, -   eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp.,     esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox,     etoxazole, etrimfos, -   fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion,     fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad,     fenpyrithrin, fenpyroximate, fenvalerate, fipronil, fluazuron,     flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,     flumethrin, flutenzine, fluvalinate, fonophos, fosmethilan,     fosthiazate, fubfenprox, furathiocarb, -   granulosis viruses, -   halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox,     hydroprene, -   imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion,     ivermectin, -   nuclear polyhedrosis viruses, -   lambda-cyhalothrin, lufenuron, -   malathion, mecarbam, metaldehyde, methamidophos, Metharhizium     anisopliae, Metharhizium flavoviride, methidathion, methiocarb,     methoprene, methomyl, methoxyfenozide, metolcarb, metoxadiazone,     mevinphos, milbemectin, milbemycin, monocrotophos, -   naled, nitenpyram, nithiazine, novaluron, -   omethoate, oxamyl, oxydemethon M, -   Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,     phenthoate, phorat, phosalone, phosmet, phosphamidon, phoxim,     pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb,     propargite, propoxur, prothiofos, prothoat, pymetrozine, pyraclofos,     pyresmethrin, pyrethrum, pyridaben, pyridathion, pyrimidifen,     pyriproxyfen, -   quinalphos, -   ribavirin, -   salithion, sebufos, silafluofen, spinosad, spirodiclofen, sulfotep,     sulprofos, -   tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,     teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,     tetrachlorvinphos, tetradifon theta-cypermethrin, thiacloprid,     thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogen oxalate,     thiodicarb, thiofanox, thuringiensin, tralocythrin, tralomethrin,     triarathene, triazamate, triazophos, triazuron, trichlophenidine,     trichlorfon, triflumuron, trimethacarb, -   vamidothion, vaniliprole, Verticillium lecanii, -   YI 5302 -   zeta-cypermethrin, zolaprofos -   (1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate, -   (3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate, -   1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine, -   2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole, -   2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione, -   2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide, -   2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide, -   3-methylphenyl propylcarbamate -   4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene, -   4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone, -   4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone, -   4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone, -   Bacillus thuringiensis strain EG-2348, -   [2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid, -   2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl     butanoate, -   [3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide, -   dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde, -   ethyl     [2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate, -   N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine, -   N-(4-chlorophenyl)-3-[4-difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide, -   N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine, -   N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide, -   N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide, -   O,O-diethyl     [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate, -   N-cyanomethyl-4-trifluoromethyl-nicotinamide, -   3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-[3-(5-trifluoromethylpyridine-2-yloxy)-propoxy]-benzene.

A mixture with other known active compounds, such as herbicides, or with fertilizers and growth regulators, is also possible.

In addition, the compounds of the formula (I) according to the invention also have very good antimycotic activity. They have a very broad antimycotic activity spectrum in particular against dermatophytes and yeasts, moulds and diphasic fungi, (for example against Candida species, such as Candida albicans, Candida glabrata), and Epidermophyton floccosum, Aspergillus species, such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species, such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The list of these fungi by no means limits the mycotic spectrum covered, but is only for illustration.

The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. Application is carried out in a customary manner, for example by watering, spraying, atomizing, broadcasting, dusting, foaming, spreading, etc. It is furthermore possible to apply the active compounds by the ultra-low volume method, or to inject the active compound preparation or the active compound itself into the soil. It is also possible to treat the seeds of the plants.

When using the active compounds according to the invention as fungicides, the application rates can be varied within a relatively wide range, depending on the kind of application. For the treatment of parts of plants, the active compound application rates are generally between 0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. For seed dressing, the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. For the treatment of the soil, the active compound application rates are generally between 0.1 and 10,000 g/ha, preferably between 1 and 5000 g/ha.

As already mentioned above, it is possible to treat all plants and their parts with active compounds according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding, such as crossing or protoplast fusion, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetical engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term “parts” or “parts of plants” or “plant parts” has been explained above.

Particularly preferably, plants of the plant cultivars which are in each case commercially available or in use are treated according to the invention. Plant cultivars are to be understood as meaning plants having new properties (“traits”) and which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive (“synergistic”) effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the substances and compositions which can be be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products are possible which exceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (i.e. those obtained by genetic engineering) which are preferably treated according to the invention include all plants which, in the genetic modification, received genetic material which imparted particularly advantageous useful properties (“traits”) to these plants. Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products. Further and particularly emphasised examples of such properties are a better defence of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active compounds. Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, cotton, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton and oilseed rape. Traits that are emphasised are in particular increased defence of the plants against insects by toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred to as “Bt plants”). Traits that are also particularly emphasised are the increased defence of the plants to fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits that are furthermore particularly, emphasised are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example the “PAT” gene). The genes which impart the desired traits in question can also be present in combination with one another in the transgenic plants. Examples of “Bt plants” which may be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylurea, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant cultivars having these genetic traits or genetic traits still to be developed, which plants will be developed and/or marketed in the future.

The plants listed can be treated according to the invention in a particularly advantageous manner with the compounds of the formula (I) according to the invention. The preferred ranges stated above for the active compounds also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds specifically mentioned in the present text.

The invention is illustrated by the examples below.

PREPARATION EXAMPLES Example 1

Process (a)

0.18 g of triethylamine is added to a solution of 0.7 g (181 mmol) of 5,7-dichloro-2-(trifluoromethyl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine and 0.28 g (1.81 mmol) of 4-trifluoromethylpiperidine in 20 ml of dichloromethane. The mixture is stirred at room temperature for 18 hours. With stirring, 1N hydrochloric acid is then added to the reaction mixture until the pH of the mixture is 1–2 (about 50 ml). The organic phase is separated off, dried over sodium sulphate and concentrated under reduced pressure. The residue is triturated with petroleum ether and filtered off with suction. This gives 0.3 g (30.3% of theory) of 5-chloro-2-(trifluoromethyl)-7-[4-trifluoromethyl)-1-piperidinyl]-6-(2,4,6-trifluorophenyl)[1,2,4]-triazolo[1,5-a]-pyrimidine.

HPLC: log P=4.43

The compounds of the formula (I) listed in Table 1 below are also obtained by methods given above.

TABLE 1 (I)

Ex. No. R¹ R² R³ R⁴ X Isomer logP m.p.: (° C.) 1 —CH₂—CH₂—CH(CF₃)—CH₂—CH₂— 2,4,6-trifluorophenyl —CF₃ Cl 4.43 2 —CH₂—CH₂—CH(CF₃)—CH₂—CH₂— 2,4,6-trifluorophenyl —C₂H₅ Cl 3.99 3 2,2,2-trifluoro-1-methylethyl —H 2,4,6-trifluorophenyl —CF₃ Cl 3.94 4 2,2,2-trifluoro-1-methylethyl —H 2,4,6-trifluorophenyl —C₂H₅ Cl 3.39 5 —CH₂—CF₃ —H 2,4,6-trifluorophenyl —C₂H₅ Cl 3.06 6 —CH₂—CH₂—CF₃ —H 2,4,6-trifluorophenyl —C₂H₅ Cl 3.18 7 —CH₂—CH₂—CF₃ —H 2,4,6-trifluorophenyl —CF₃ Cl 3.76 8 —CH₂—CF₃ —H 2,4,6-trifluorophenyl —CF₃ Cl 3.64 9 2,2,2-trifluoro-1-methylethyl —H 2,4,6-trifluorophenyl t-butyl Cl 4.24 10 —CH₂—C(CH₃)═CH₂ —C₂H₅ 2,4,6-trifluorophenyl —CF₃ Cl 4.73 11 -isopropyl —H 2,4,6-trifluorophenyl —CF₃ Cl 3.8 12 2,2,2-trifluoro-1-methylethyl —H 2,4,6-trifluorophenyl —CH₃ Cl 3.01 13 —CH₂—CF₃ —H 2,4,6-trifluorophenyl —CH₃ Cl 2.69 14 —CH₂—C(CH₃)═CH₂ —C₂H₅ 2,4,6-trifluorophenyl —CH₃ Cl 3.83 15 —CH₂—C(CH₃)═CH₂ —C₂H₅ 2,4,6-trifluorophenyl —C₂H₅ Cl 4.34 16 —CH₂—C(CH₃)═CH₂ —H 2,4,6-trifluorophenyl —CH₃ Cl 2.76 17 -isopropyl —H 2-chlorophenyl cyclopropyl Cl 3.39 18 —CH₂—CN —H 2,4,6-trifluorophenyl —CH₃ Cl 2.02 19 2,2,2-trifluoro-1-methylethyl —H 2-chlorophenyl cyclopropyl Cl AS 3.59 20 2,2,2-trifluoro-1-methylethyl —H 2-chlorophenyl cyclopropyl Cl BS 3.61 21 —CH₂—C(CH₃)═CH₂ —H 2,4,6-trifluorophenyl —C₂H₅ Cl 3.15 22 —CH₂—C(CH₃)═CH₂ —H 2,4,6-trifluorophenyl —CF₃ Cl 3.82 23 —CH₂—CN —H 2,4,6-trifluorophenyl —C₂H₅ Cl 2.27 24 —CH₂—CN —H 2,4,6-trifluorophenyl —CF₃ Cl 2.91 25 2,2,2-trifluoro-1-methylethyl —H 2,4,6-trifluorophenyl —CF₃ Br 3.99 26 -isopropyl —H 2,4,6-trifluorophenyl —CH₃ Cl 2.71 27 —NH₂ -isopropyl 2,4,6-trifluorophenyl —CH₃ Cl 2 77 28 isopropylamino —H 2,4,6-trifluorophenyl —CH₃ Cl 2.7 29 2-methoxyethyl —C₂H₅ 2,4,6-trifluorophenyl —CH₃ Cl 2.93 30 2-methoxyethyl —C₂H₅ 2,4,6-trifluorophenyl —C₂H₅ Cl 3.37 31 2-methoxyethyl —C₂H₅ 2,4,6-trifluorophenyl —CF₃ Cl 4.04 32 cyclopentyl —H 2,4,6-trifluorophenyl —CF₃ Cl 4.25 33 —C₂H₅ —C₂H₅ 2,4,6-trifluorophenyl —CF₃ Cl 4.25 34 —CH₂—CH₂—O—CH₂—CH₂— 2,4,6-trifluorophenyl —CF₃ Cl 3.22 35 cyclopropyl —H 2,4,6-trifluorophenyl —CF₃ Cl 3.53 36 —CH₃ —CH₃ 2-chlorophenyl cyclopropyl Cl 3.13 37 —C₂H₅ —H 2-chlorophenyl cyclopropyl Cl 38 —CH₂—CH₂—CH₂—CH₂— 2-chlorophenyl cyclopropyl Cl 39 —CH₂—CN —H 2-chlorophenyl cyclopropyl Cl 40 cyclopentyl —H 2-chlorophenyl cyclopropyl Cl 41 —C₂H₅ —C₂H₅ 2-chlorophenyl cyclopropyl Cl 42 —CH₂—CH₂—O—CH₂—CH₂— 2-chlorophenyl cyclopropyl Cl 43 2-methoxyethyl —H 2-chlorophenyl cyclopropyl Cl 44 —CH₃ —H 2-chlorophenyl cyclopropyl Cl 45 —CH₂—CH₂—S—CH₂—CH₂— 2-chlorophenyl cyclopropyl Cl 46 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chlorophenyl cyclopropyl Cl 47 cyclohexyl —H 2-chlorophenyl cyclopropyl Cl 48 cyclopropylmethyl —H 2-chlorophenyl cyclopropyl Cl 49 isopropylamino —H 2,4,6-trifluorophenyl —C₂H₅ Cl 3.05 50 1-cyclopropylethylamino —H 2-chlorophenyl cyclopropyl Cl 51 n-butylamino —H 2-chlorophenyl cyclopropyl Cl 52 —NH—CH₂—CF₂—CHF₂ —H 2-chlorophenyl cyclopropyl Cl 53 —NH—CH₂—CH(CH₃)₂ —H 2-chlorophenyl cyclopropyl Cl 54 allylamino —H 2-chlorophenyl cyclopropyl Cl 55 —NH—CH₂—CF₃ —H 2-chlorophenyl cyclopropyl Cl 56 isopropylamino —H 2-chlorophenyl cyclopropyl Cl 57 t-butylamino —H 2-chlorophenyl cyclopropyl Cl 58 —CH₂—CH(CH₃)—O—CH(CH₃)—CH₂— 2,4,6-trifluorophenyl —CH₃ Cl 3 59 —CH₂—CH₂—CH₂—CH₂— 2,4,6-trifluorophenyl —CH₃ Cl 2.86 60 —CH₂—CH₂—CH₂—CH₂—CH₂— 2,4,6-trifluorophenyl —CH₃ Cl 3.43 61 n-propyl —H 2,4,6-trifluorophenyl —CH₃ Cl 2.75 62 cyclopentyl —H 2,4,6-trifluorophenyl —CH₃ Cl 3.23 63 —C₂H₅ —C₂H₅ 2,4,6-trifluorophenyl —CH₃ Cl 3.23 64 2-methoxyethyl —H 2,4,6-trifluorophenyl —CH₃ Cl 2.34 65 cyclopropyl —H 2,4,6-trifluorophenyl —CH₃ Cl 2.51 66 —CH₂—CH₂—S—CH₂—CH₂— 2,4,6-trifluorophenyl —CH₃ Cl 3.09 67 —CH₂—CH₂—CH(CF₃)—CH₂—CH₂— 2,4,6-trifluorophenyl —CH₃ Cl 3.6 68 cyclopropylmethyl —H 2,4,6-trifluorophenyl —CH₃ Cl 2.86 69 2,2,2-trifluoro-1-methylethyl —H 2,4,6-trifluorophenyl —CH₃ Cl 3.04 70 —CH₂—CH₂—CF₃ —H 2,4,6-trifluorophenyl —CH₃ Cl 2.85 71 —CH₂—CH(CH₃)—O—CH(CH₃)—CH₂— 2,4,6-trifluorophenyl —C₂H₅ Cl 3.57 72 —CH₂—CH₂—CH₂—CH₂— 2,4,6-trifluorophenyl —C₂H₅ Cl 3.29 73 —CH₂—CH₂—CH₂—CH₂—CH₂— 2,4,6-trifluorophenyl —C₂H₅ Cl 3.94 74 n-propyl —H 2,4,6-trifluorophenyl —C₂H₅ Cl 3.14 75 cyclopentyl —H 2,4,6-trifluorophenyl —C₂H₅ Cl 3.66 76 -isopropyl —H 2,4,6-trifluorophenyl —C₂H₅ Cl 3.15 77 —C₂H₅ —C₂H₅ 2,4,6-trifluorophenyl —C₂H₅ Cl 3.71 78 2-methoxyethyl —H 2,4,6-trifluorophenyl —C₂H₅ Cl 2.68 79 cyclopropyl —H 2,4,6-trifluorophenyl —C₂H₅ Cl 2.85 80 —CH₂—CH₂—S—CH₂—CH₂— 2,4,6-trifluorophenyl —C₂H₅ Cl 3.53 81 cyclopropylmethyl —H 2,4,6-trifluorophenyl —C₂H₅ Cl 3.23 82 -isopropyl —H 3-chloro-4-fluorophenyl —CH₃ Cl 3.01 83 —CH₂—CH₂—CH═CH—CH₂— 2,4,6-trifluorophenyl —CH₃ Cl 3.2 84 isopropylamino —H 2,4,6-trifluorophenyl —CF₃ Cl 3.68 85 —CH₂—CH₂—CH═C(CH₃)—CH₂— 2,4,6-trifluorophenyl —CH₃ Cl 3.57 86 —CH₃ —CH₃ 2,4,6-trifluorophenyl —CH₃ Cl 2.49 87 —C₂H₅ —H 2,4,6-trifluorophenyl —CH₃ Cl 2.44 88 —C(CH₃)₂—CF₃ —H 2,4,6-trifluorophenyl —CH₃ Cl 3.7 89 —CH₂—CH₂—O—CH₂—CH₂— 2,4,6-trifluorophenyl —CH₃ Cl 2.43 90 —CH₃ —H 2,4,6-trifluorophenyl —CH₃ Cl 2.12 91 —C₂H₅ —H 2,4,6-trifluorophenyl —C₂H₅ Cl 2.78 92 —CH₂—CH₂—O—CH₂—CH₂— 2,4,6-trifluorophenyl —C₂H₅ Cl 2.8 93 —CH₃ —H 2,4,6-trifluorophenyl —C₂H₅ Cl 2.44 94 —CH(CF₃)—CH₂—CH₂—CH₂—CH₂— 2,4,6-trifluorophenyl —C₂H₅ Cl 4.27 95 —CH₂—C(CH₃)═CH₂ —C₂H₅ 2,4,6-trifluorophenyl —CF₃ Cl 4.69 123–25 96 —CH₂—C(CH₃)═CH₂ —C₂H₅ 2,4-difluorophenyl —CH₃ Cl 3.73 100–02 97 2,2,2-trifluoro-1-methylethyl —H 3-chloro-4-fluorophenyl —CH₃ Cl 3.32 98 —CH₂—CH(OH)—CH₂—CH₂— 2,4,6-trifluorophenyl —CH₃ Cl 1.85 99 —CH₂—CH(OH)—CH₂—CH₂—CH₂— 2,4,6-trifluorophenyl —CH₃ Cl 2.15 100 —CH₃ —CH₃ 2,4,6-trifluorophenyl —CF₃ Cl 3.6 101 —CH₂—CH(CH₃)—O—CH(CH₃)—CH₂— 2,4,6-trifluorophenyl —CF₃ Cl 4.18 102 —C₂H₅ —H 2,4,6-trifluorophenyl —CF₃ Cl 3.5 103 —CH₂—CH₂—CH₂—CH₂— 2,4,6-trifluorophenyl —CF₃ Cl 3.92 104 —CH₂—CH₂—CH₂—CH₂—CH₂— 2,4,6-trifluorophenyl —CF₃ Cl 4.46 105 —C(CH₃)₂—CF₃ —H 2,4,6-trifluorophenyl —CF₃ Cl 4.37 106 n-propyl —H 2,4,6-trifluorophenyl —CF₃ Cl 3.82 107 2-methoxyethyl —H 2,4,6-trifluorophenyl —CF₃ Cl 3.38 108 —CH₃ —H 2,4,6-trifluorophenyl —CF₃ Cl 3.17 109 —CH(CF₃)—CH₂—CH₂—CH₂—CH₂— 2,4,6-trifluorophenyl —CF₃ Cl 4.76 110 —CH₂—CH₂—S—CH₂—CH₂— 2,4,6-trifluorophenyl —CF₃ Cl 4.09 111 cyclopropylmethyl —H 2,4,6-trifluorophenyl —CF₃ Cl 3.89 112 —CH₂—S—CH₂—CH₂— 2,4,6-trifluorophenyl —CH₃ Cl 2.84 113 2,2,2-trifluoro-1-methylethyl —H 2,4,6-trifluorophenyl —CH₃ Cl 3.03 114 —CH₂—C(CH₃)═CH₂ —C₂H₅ 2-chloro-6-fluorophenyl —CH₃ Cl 3.91 115 —CH(CH₂OH)—COOCH₃ —H 2,4,6-trifluorophenyl —CH₃ Cl 1.93 116 —CH(CH₃)—CH₂—O—CH₃ —H 2,4,6-trifluorophenyl —CH₃ Cl 2.64 117 —CH(CH₃)—CH═CH—CH(CH₃)— 2,4,6-trifluorophenyl —CH₃ Cl 3.52 118 AB3 —H 2,4,6-trifluorophenyl —CH₃ Cl 3.11 119 AB4 2,4,6-trifluorophenyl —CH₃ Cl 2.65 120 AB5 —H 2,4,6-trifluorophenyl —CH₃ Cl 3.47 121 AB6 2,4,6-trifluorophenyl —CH₃ Cl 2.13 122 —CH(CH₃)—CH₂—OH —H 2,4,6-trifluorophenyl —CH₃ Cl 1.93 123 —CH(CH₃)—CH(O—CH₃)₂ —H 2,4,6-trifluorophenyl —CH₃ Cl 2.74 124 —CH(CH₃)—COOCH₃ —H 2,4,6-trifluorophenyl —CH₃ Cl 2.45 125 —CH₂—COOCH₃ —H 2,4,6-trifluorophenyl —CH₃ Cl 2.13 126 —CH(CH₃)—COO-t-butyl —H 2,4,6-trifluorophenyl —CH₃ Cl 3.44 127 —NH₂ isobutyl 2,4,6-trifluorophenyl —C₂H₅ Cl 3.47 176–78 128 2-methoxyethyl —C₂H₅ 2,4-difluorophenyl —CH₃ Cl 2.84 129 —NH₂ isobutyl 2,4,6-trifluorophenyl —CH₃ Cl 3.06 paste 130 —NH₂ isobutyl 2-chloro-6-fluorophenyl —CH₃ Cl 3.12 157–8 131 —NH₂ isobutyl 3-chloro-4-fluorophenyl —CH₃ Cl 3.31 155–8 132 2,2,2-trifluoro-1-methylethyl —H 2-chloro-6-fluorophenyl —CH₃ Cl 3.01 133 —CH₂—C(CH₃)═CH₂ —C₂H₅ 2-chlorophenyl —CH₃ Cl 3.9 134 1,2-Dimethylpropyl —H 2,4,6-trifluorophenyl —CH₃ Cl 3.37 135 i-Butoxy —H 2,6-difluorophenyl —CH₃ Cl 2.88 136 —O—C₂H₅ —H 2,6-difluorophenyl —CH₃ Cl 2.22 137 3-chlorobenzyloxy —H 2,6-difluorophenyl —CH₃ Cl 3.21 138 4-chlorobenzyloxy —H 2,6-difluorophenyl —CH₃ Cl 3.23 139 —O—CH(CH₃)—CH₂—CH₃ —H 2,6-difluorophenyl —CH₃ Cl 2.78 140 allyloxy —H 2,6-difluorophenyl —CH₃ Cl 2.38 141 t-butoxy —H 2,6-difluorophenyl —CH₃ Cl 2.68 142 2-hexahydropyranyloxy —H 2,6-difluorophenyl —CH₃ Cl 2.54 143 —O—CH₃ —CH₃ 2,6-difluorophenyl —CH₃ Cl 2.54 144 O-isopropyl —H 2,6-difluorophenyl —CH₃ Cl 2.46 145 isobutyl —H 2,4,6-trifluorophenyl —CH₃ Cl 3.14 146 —CH₂—C(CH₃)₃ —H 2,4,6-trifluorophenyl —CH₃ Cl 3.5 147 2-butyl —H 2,4,6-trifluorophenyl —CH₃ Cl 3.1 148 —CH₂—CH₂—N(CH₃)₂ —CH₃ 2,4,6-trifluorophenyl —CH₃ Cl 1.5 149 propargyl —CH₃ 2,4,6-trifluorophenyl —CH₃ Cl 2.77 150 —CH₂—COOC₂H₅ —CH₃ 2,4,6-trifluorophenyl —CH₃ Cl 2.8 151 1,3-dioxolan-2-ylmethyl —CH₃ 2,4,6-trifluorophenyl —CH₃ Cl 2.67 152 allyl —CH₃ 2,4,6-trifluorophenyl —CH₃ Cl 3.18 153 (2-furyl)methyl —CH₃ 2,4,6-trifluorophenyl —CH₃ Cl 3.22 154 isobutyl —CH₃ 2,4,6-trifluorophenyl —CH₃ Cl 3.63 155 —CH₂—C(CH₃)═CH₂ —CH₃ 2,4,6-trifluorophenyl —CH₃ Cl 3.55 156 —CH₂—CH₂—N(CH₃)₂ —C₂H₅ 2,4,6-trifluorophenyl —CH₃ Cl 1.59 157 allyl —C₂H₅ 2,4,6-trifluorophenyl —CH₃ Cl 3.5 158 (2-furyl)methyl —C₂H₅ 2,4,6-trifluorophenyl —CH₃ Cl 3.55 159 (2-tetrahydrofuryl)methyl —C₂H₅ 2,4,6-trifluorophenyl —CH₃ Cl 3.26 160 —CH₂—COOC₂H₅ —C₂H₅ 2,4,6-trifluorophenyl —CH₃ Cl 3.14 161 n-butyl —C₂H₅ 2,4,6-trifluorophenyl —CH₃ Cl 4.08 162 cyclopropylmethyl n-propyl 2,4,6-trifluorophenyl —CH₃ Cl 4.08 163 (2-tetrahydrofuryl)methyl n-propyl 2,4,6-trifluorophenyl —CH₃ Cl 3.68 164 —CH₂—CH₂—CH₂—CH₂CH(CH₃)— 2,4,6-trifluorophenyl —CH₃ Cl 3.81 165 —CH₂—CH₂—CH₂—CH(CH₃)—CH₂— 2,4,6-trifluorophenyl —CH₃ Cl 3.9 166 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4,6-trifluorophenyl —CH₃ Cl 3.9 167 —CH₂—CH₂—CHF—CH₂—CH₂— 2,4,6-trifluorophenyl —CH₃ Cl 3.03 168 AB7 2,4,6-trifluorophenyl —CH₃ Cl 3.73 169 —CH₂—CH(CH₃)—O—CH(CH₃)—CH₂— 2,6-difluorophenyl —CH₃ Cl 2.84 170 —CH₂—CH₂—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 2.61 171 —CH₂—CH₂—CH₂—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 3.17 172 n-propyl —H 2,6-difluorophenyl —CH₃ Cl 2.52 173 cyclopentyl —H 2,6-difluorophenyl —CH₃ Cl 2.97 174 -isopropyl —H 2,6-difluorophenyl —CH₃ Cl 2.52 175 —C₂H₅ —C₂H₅ 2,6-difluorophenyl —CH₃ Cl 2.98 176 —CH₂—CH₂—O—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 2.2 177 2-methoxyethyl —H 2,6-difluorophenyl —CH₃ Cl 2.12 178 cyclopropyl —H 2,6-difluorophenyl —CH₃ Cl 2.28 179 —CH₂—CH₂—S—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 2.84 180 —CH₂—CH₂—CH(CF₃)—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 3.36 181 cyclopropylmethyl —H 2,6-difluorophenyl —CH₃ Cl 2.62 182 2,2,2-trifluoro-1-methylethyl —H 2,6-difluorophenyl —CH₃ Cl 2.78 183 —CH₂—C(CH₃)═CH₂ —H 2,6-difluorophenyl —CH₃ Cl 2.56 184 —CH₂—CH₂—CF₃ —H 2,6-difluorophenyl —CH₃ Cl 2.63 185 1-cyclohexylethyl —H 2,6-difluorophenyl —CH₃ Cl 4 186 cyclohexyl —H 2,6-difluorophenyl —CH₃ Cl 3.28 187 2-butyl —H 2,6-difluorophenyl —CH₃ Cl 2.82 188 3-trifluoromethylcyclohexyl —H 2,6-difluorophenyl —CH₃ Cl 3.37 189 3,5-bis-trifluoromethylcyclohexyl —H 2,6-difluorophenyl —CH₃ Cl 3.62 190 4-trifluoromethylcyclohexyl —H 2,6-difluorophenyl —CH₃ Cl 3.39 191 isobutyl —H 2,4-difluorophenyl —CH₃ Cl 3 192 n-butyl —H 2,4-difluorophenyl —CH₃ Cl 3.04 193 —CH₂—C(CH₃)₃ —H 2,4-difluorophenyl —CH₃ Cl 3.4 194 2-butyl —H 2,4-difluorophenyl —CH₃ Cl 3.01 195 —CH₂—CH₂—CF₃ —H 2,4-difluorophenyl —CH₃ Cl 2.76 196 -isopropyl —H 2,4-difluorophenyl —CH₃ Cl 2.69 197 cyclohexyl —H 2,4-difluorophenyl —CH₃ Cl 3.46 198 1-cyclohexylethyl —H 2,4-difluorophenyl —CH₃ Cl 4.24 199 cyclopropyl —H 2,4-difluorophenyl —CH₃ Cl 2.45 200 cyclopropylmethyl —H 2,4-difluorophenyl —CH₃ Cl 2.77 201 —CH₂—C(CH₃)═CH₂ —H 2,4-difluorophenyl —CH₃ Cl 2.72 202 1,3-dioxolan-2-ylmethyl —CH₃ 2,4-difluorophenyl —CH₃ Cl 2.56 203 allyl —CH₃ 2,4-difluorophenyl —CH₃ Cl 3.06 204 (2-furyl)methyl —CH₃ 2,4-difluorophenyl —CH₃ Cl 3.1 205 isobutyl —CH₃ 2,4-difluorophenyl —CH₃ Cl 3.49 206 —CH₂—C(CH₃)═CH₂ —CH₃ 2,4-difluorophenyl —CH₃ Cl 3.41 207 allyl —C₂H₅ 2,4-difluorophenyl —CH₃ Cl 3.35 208 (2-tetrahydrofuryl)methyl —C₂H₅ 2,4-difluorophenyl —CH₃ Cl 3.18 209 2-methoxyethyl n-propyl 2,4-difluorophenyl —CH₃ Cl 3.26 210 isobutyl —H 2-chlorophenyl —CH₃ Cl 3.1 211 —CH₂—C(CH₃)₃ —H 2-chlorophenyl —CH₃ Cl 3.57 212 2-butyl —H 2-chlorophenyl —CH₃ Cl 3.09 213 cyclopentyl —H 2-chlorophenyl —CH₃ Cl 3.28 214 -isopropyl —H 2-chlorophenyl —CH₃ Cl 2.75 215 cyclopropyl —H 2-chlorophenyl —CH₃ Cl 2.54 216 cyclopropylmethyl —H 2-chlorophenyl —CH₃ Cl 2.85 217 —CH₂—C(CH₃)═CH₂ —H 2-chlorophenyl —CH₃ Cl 2.83 218 —CH(CH₃)—CH₂—CH(CH₃)₂ —H 2-chlorophenyl —CH₃ Cl 3.84 219 1,3-dioxolan-2-ylmethyl —CH₃ 2-chlorophenyl —CH₃ Cl 2.62 220 allyl —CH₃ 2-chlorophenyl —CH₃ Cl 3.19 221 isobutyl —CH₃ 2-chlorophenyl —CH₃ Cl 3.65 222 2-methoxyethyl —CH₃ 2-chlorophenyl —CH₃ Cl 2.64 223 —CH₂—C(CH₃)═CH₂ —CH₃ 2-chlorophenyl —CH₃ Cl 3.57 224 allyl —C₂H₅ 2-chlorophenyl —CH₃ Cl 3.5 225 2-methoxyethyl —C₂H₅ 2-chlorophenyl —CH₃ Cl 2.94 226 —CH₂—CH₂—CH₂—CH(CH₃)— 2-chlorophenyl —CH₃ Cl 3.27 227 —CH₂—CH₂—CH₂—CH₂— 2-chlorophenyl —CH₃ Cl 0.75 228 —CH₂—CH₂—CH═CH—CH₂— 2-chlorophenyl —CH₃ Cl 0.75 229 —CH₂—CH₂—CH₂—CH(CH₃)—CH₂— 2-chlorophenyl —CH₃ Cl 3.92 230 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chlorophenyl —CH₃ Cl 3.94 231 —CH₂—CH₂—CH═C(CH₃)—CH₂— 2-chlorophenyl —CH₃ Cl 3.7 232 —CH₂—CH₂—CH(CF₃)—CH₂—CH₂— 2-chlorophenyl —CH₃ Cl 3.63 233 —CH₂—CH₂—CH₂—CH₂—CH₂— 2-chlorophenyl —CH₃ Cl 3.48 234 —CH₂—CH₂—O—CH₂—CH₂— 2-chlorophenyl —CH₃ Cl 2.38 235 —CH₂—CH₂—S—CH₂—CH₂— 2-chlorophenyl —CH₃ Cl 3.09 236 2-methoxyethyl —H 2-chlorophenyl —CH₃ Cl 2.3 237 propargyl —CH₃ 2-chlorophenyl —CH₃ Cl 2.75 238 (2-furyl)methyl —CH₃ 2-chlorophenyl —CH₃ Cl 3.2 239 (2-tetrahydrofuryl)methyl —C₂H₅ 2-chlorophenyl —CH₃ Cl 3.23 240 —CH₂—COOC₂H₅ —C₂H₅ 2-chlorophenyl —CH₃ Cl 3.11 241 n-butyl —C₂H₅ 2-chlorophenyl —CH₃ Cl 4.1 242 C₂H₅ —C₂H₅ 2-chlorophenyl —CH₃ Cl 3.24 243 cyclopropylmethyl n-propyl 2-chlorophenyl —CH₃ Cl 4.07 244 (2-tetrahydrofuryl)methyl n-propyl 2-chlorophenyl —CH₃ Cl 3.7 245 —CH₂—CH(OH)—CH₂—CH₂— 2-chlorophenyl —CH₃ Cl 0.75 246 —CH₂—CH₂—O—CH₂—CH₂— 2-chloro-6-fluorophenyl —CH₃ Cl 2.48 247 n-butyl —C₂H₅ 2-chlorophenyl —CH₃ Cl 4.18 248 isobutyl —H 2-chloro-6-fluorophenyl —CH₃ Cl 3.14 249 —CH₂—C(CH₃)₃ —H 2-chloro-6-fluorophenyl —CH₃ Cl 3.59 250 —CH₂—C(CH₃)═CH₂ —H 2-chloro-6-fluorophenyl —CH₃ Cl 2.8 251 —CH₂—CH₂—CH₂—CH₂— 2-chloro-6-fluorophenyl —CH₃ Cl 2.95 252 —C₂H₅ —C₂H₅ 2-chloro-6-fluorophenyl —CH₃ Cl 3.33 253 —CH₂—CN —H 2-chloro-6-fluorophenyl —CH₃ Cl 2.11 254 —CH₂—CH₂—CH₂—CH₂—CH₂— 2-chloro-6-fluorophenyl —CH₃ Cl 3.55 255 cyclopentyl —H 2-chloro-6-fluorophenyl —CH₃ Cl 3.29 256 -isopropyl —H 2-chloro-6-fluorophenyl —CH₃ Cl 2.77 257 2-methoxyethyl —H 2-chloro-6-fluorophenyl —CH₃ Cl 2.42 258 cyclopropyl —H 2-chloro-6-fluorophenyl —CH₃ Cl 2.77 259 —CH₂—CH₂—S—CH₂—CH₂— 2-chloro-6-fluorophenyl —CH₃ Cl 3.18 260 —CH₂—CF₃ —H 2-chloro-6-fluorophenyl —CH₃ Cl 2.77 261 —CH₂—CH₂—CH(CF₃)—CH₂—CH₂— 2-chloro-6-fluorophenyl —CH₃ Cl 3.72 262 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-6-fluorophenyl —CH₃ Cl 3.99 263 cyclopropylmethyl —H 2-chloro-6-fluorophenyl —CH₃ Cl 2.95 264 2-butyl —H 2-chloro-6-fluorophenyl —CH₃ Cl 3.14 265 —CH₂—CH₂—CH═CH—CH₂— 2-chloro-6-fluorophenyl —CH₃ Cl 3.33 266 —CH₂—CH₂—CHF—CH₂—CH₂— 2-chloro-6-fluorophenyl —CH₃ Cl 3.07 267 allyl —C₂H₅ 2-chloro-6-fluorophenyl —CH₃ Cl 3.59 268 (2-tetrahydrofuryl)methyl —C₂H₅ 2-chloro-6-fluorophenyl —CH₃ Cl 3.29 269 2-methoxyethyl —C₂H₅ 2-chloro-6-fluorophenyl —CH₃ Cl 3.03 270 —CH₂—COOC₂H₅ —C₂H₅ 2-chloro-6-fluorophenyl —CH₃ Cl 3.14 271 propargyl —CH₃ 2-chloro-6-fluorophenyl —CH₃ Cl 2.77 272 —CH₂—COOC₂H₅ —CH₃ 2-chloro-6-fluorophenyl —CH₃ Cl 2.48 273 allyl —CH₃ 2-chloro-6-fluorophenyl —CH₃ Cl 3.26 274 (2-furyl)methyl —CH₃ 2-chloro-6-fluorophenyl —CH₃ Cl 3.26 275 —CH₂—C(CH₃)═CH₂ —CH₃ 2-chloro-6-fluorophenyl —CH₃ Cl 3.63 276 isobutyl —CH₃ 2-chloro-6-fluorophenyl —CH₃ Cl 3.68 277 (2-tetrahydrofuryl)methyl n-Propyl 2-chloro-6-fluorophenyl —CH₃ Cl 3.72 278 —CH₂—CH(OH)—CH₂—CH₂— 2-chloro-6-fluorophenyl —CH₃ Cl 2.02 279 1,3-dioxolan-2-ylmethyl —CH₃ 2-chloro-6-fluorophenyl —CH₃ Cl 280 —CH₂—CH₂—CH₂—CH(CH₃)— 2,4-difluorophenyl —CH₃ Cl 3.14 281 —CH₂—CH₂—CH₂—CH₂— 2,4-difluorophenyl —CH₃ Cl 2.74 282 —CH₂—CH₂—CH(OH)—CH₂—CH₂— 2,4-difluorophenyl —CH₃ Cl 1.9 283 —CH₂—CH₂—CH═CH—CH₂— 2,4-difluorophenyl —CH₃ Cl 3.11 284 AB10 2,4-difluorophenyl —CH₃ Cl 2.68 285 —CH₂—CH₂—CH₂—CH₂—CH(CH₃)— 2,4-difluorophenyl —CH₃ Cl 3.7 286 —CH₂—CH₂—CH₂—CH(CH₃)—CH₂— 2,4-difluorophenyl —CH₃ Cl 3.74 287 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4-difluorophenyl —CH₃ Cl 3.75 288 —CH₂—CH₂—C(CH₃)₂—CH₂—CH₂— 2,4-difluorophenyl —CH₃ Cl 4.01 289 —CH₂—CH₂—CH(COCH₃)—CH₂—CH₂— 2,4-difluorophenyl —CH₃ Cl 2.5 290 —CH₂—CH═C(C₂H₅)—CH₂—CH₂— 2,4-difluorophenyl —CH₃ Cl 3.94 291 —CH₂—CH₂—CH═C(CH₃)—CH₂— 2,4-difluorophenyl —CH₃ Cl 3.49 292 —CH₂—CH₂—CH(COOCH₃)—CH₂—CH₂— 2,4-difluorophenyl —CH₃ Cl 2.78 293 —CH₂—CH₂—CH(CF₃)—CH₂—CH₂— 2,4-difluorophenyl —CH₃ Cl 3.49 294 —CH₂—CH₂—CH(NH—COCH₃)—CH₂—CH₂— 2,4-difluorophenyl —CH₃ Cl 1.85 295 —CH₂—CH₂—CH₂—CH₂—CH₂— 2,4-difluorophenyl —CH₃ Cl 3.32 296 —CH₂—CH₂—O—CH₂—CH₂— 2,4-difluorophenyl —CH₃ Cl 2.3 297 —CH₂—CH₂—S—CH₂—CH₂— 2,4-difluorophenyl —CH₃ Cl 2.97 298 4-tolyl —H 2,4-difluorophenyl —CH₃ Cl 3.05 299 4-fluorophenyl —H 2,4-difluorophenyl —CH₃ Cl 2.7 300 AB13 2,4-difluorophenyl —CH₃ Cl 3.28 301 —CH(CH₃)—CH₂—CH(CH₃)₂ —H 2,4-difluorophenyl —CH₃ Cl 3.7 302 —CH₂—CH₂—CH₂—CH(CH₃)—CH₂— 2-chloro-6-fluorophenyl —CH₃ Cl 3.99 303 —CH₂—CH(OH)—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 1.73 304 —CH₂—CH₂—CH₂—CH(CH₃)— 2,6-difluorophenyl —CH₃ Cl 3.02 305 AB8 2,6-difluorophenyl —CH₃ Cl 1.64 306 AB9 2,6-difluorophenyl —CH₃ Cl 1.18 307 —CH₂—CH₂—CH(OH)—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 1.83 308 —CH₂—CH₂—CH═CH—CH₂— 2,6-difluorophenyl —CH₃ Cl 3.01 309 AB10 2,6-difluorophenyl —CH₃ Cl 2.6 310 —CH₂—CH(CH₃)—CH₂—CH(CH₃)—CH₂— 2,6-difluorophenyl —CH₃ Cl 4.08 311 —CH₂—CH₂—CH₂—CH₂—CH(CH₃)— 2,6-difluorophenyl —CH₃ Cl 3.57 312 —CH₂—CH₂—CH₂—CH(CH₃)—CH₂— 2,6-difluorophenyl —CH₃ Cl 3.63 313 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 3.64 314 —CH₂—CH(OH)—CH₂—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 2.03 315 —CH₂—CH₂—C(CH₃)₂—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 3.91 316 —CH₂—CH═C(C₂H₅)—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 3.84 317 —CH₂—CH₂—CH═C(CH₃)—CH₂— 2,6-difluorophenyl —CH₃ Cl 3.39 318 —CH₂—CH₂—CH(COOCH₃)—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 2.69 319 —CH_(2—CH) ₂—CHBr—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 3.33 320 —CH(COOCH₃)—CH₂—CH₂—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 3.04 321 AB12 2,6-difluorophenyl —CH₃ Cl 3.15 322 AB11 2-fluorophenyl —CH₃ Cl 1.26 323 —CH₂—CH₂—CH(NH—COCH₃)—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 1.78 324 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 1.12 325 AB14 2,6-difluorophenyl —CH₃ Cl 3.56 326 3-tolyl —H 2,6-difluorophenyl —CH₃ Cl 2.89 327 AB13 2,6-difluorophenyl —CH₃ Cl 3.22 328 isobutyl —H 2,6-difluorophenyl —CH₃ Cl 2.85 329 —CH₂—C(CH₃)₃ —H 2,6-difluorophenyl —CH₃ Cl 3.27 330 —CH(CH₃)—CH₂—CH(CH₃)₂ —H 2,6-difluorophenyl —CH₃ Cl 3.55 331 propargyl —CH₃ 2,6-difluorophenyl —CH₃ Cl 2.54 332 1,3-dioxolan-2-ylmethyl —CH₃ 2,6-difluorophenyl —CH₃ Cl 2.43 333 allyl —CH₃ 2,6-difluorophenyl —CH₃ Cl 2.95 334 —CH₂—CH(OCH₃)₂ —CH₃ 2,6-difluorophenyl —CH₃ Cl 2.55 335 isobutyl —CH₃ 2,6-difluorophenyl —CH₃ Cl 3.37 336 2-methoxyethyl —CH₃ 2,6-difluorophenyl —CH₃ Cl 2.45 337 —CH₂—C(CH₃)═CH₂ —CH₃ 2,6-difluorophenyl —CH₃ Cl 3.3 338 n-butyl —CH₃ 2,6-difluorophenyl —CH₃ Cl 3.46 339 —CH₂—C(CH₃)═CH₂ —C₂H₅ 2,6-difluorophenyl —CH₃ Cl 3.65 340 (2-furyl)methyl —C₂H₅ 2,6-difluorophenyl —CH₃ Cl 3.28 341 (2-tetrahydrofuryl)methyl —C₂H₅ 2,6-difluorophenyl —CH₃ Cl 3 342 2-methoxyethyl —C₂H₅ 2,6-difluorophenyl —CH₃ Cl 2.74 343 —CH₂—COOC₂H₅ —C₂H₅ 2,6-difluorophenyl —CH₃ Cl 2.85 344 n-butyl —C₂H₅ 2,6-difluorophenyl —CH₃ Cl 3.82 345 cyclopropylmethyl n-propyl 2,6-difluorophenyl —CH₃ Cl 3.83 346 (2-tetrahydropyranyl)methyl n-propyl 2,6-difluorophenyl —CH₃ Cl 3.95 347 (2-tetrahydrofuryl)methyl n-propyl 2,6-difluorophenyl —CH₃ Cl 3.39 348 2-methoxyethyl n-propyl 2,6-difluorophenyl —CH₃ Cl 3.12 349 3-trifluoromethylcyclohexyl —H 2,4-difluorophenyl —CH₃ Cl 3.52 350 —CH₂—CH₂—N(CH₃)₂ —CH₃ 2,4-difluorophenyl —CH₃ Cl 1.23 351 propargyl —CH₃ 2,4-difluorophenyl —CH₃ Cl 2.67 352 2-methoxyethyl —CH₃ 2,4-difluorophenyl —CH₃ Cl 2.58 353 —CH₂—CH₂—N(CH₃)₂ —C₂H₅ 2,4-difluorophenyl —CH₃ Cl 1.37 354 (2-furyl)methyl —C₂H₅ 2,4-difluorophenyl —CH₃ Cl 3.39 355 —CH₂—COOC₂H₅ —C₂H₅ 2,4-difluorophenyl —CH₃ Cl 3.04 356 cyclopropylmethyl n-propyl 2,4-difluorophenyl —CH₃ Cl 3.91 357 (2-tetrahydrofuryl)methyl n-propyl 2,4-difluorophenyl —CH₃ Cl 3.6 358 2,2,2-trifluoro-1-methylethyl —H 2,4-difluorophenyl —CF₃ Cl 3.89 359 2,2,2-trifluoro-1-methylethyl —H 2,4-difluorophenyl —CH₃ Cl AS 2.95 360 2,2,2-trifluoro-1-methylethyl —H 2,4-difluorophenyl —CH₃ Cl BS 2.96 361 isobutoxy —H 2-fluorophenyl —CH₃ Cl 2.98 362 —O—C₂H₅ —H 2-fluorophenyl —CH₃ Cl 2.28 363 benzyloxy —H 2-fluorophenyl —CH₃ Cl 2.93 364 3,5-dichlorobenzyloxy —H 2-fluorophenyl —CH₃ Cl 3.76 365 4-trifluoromethylbenzyloxy —H 2-fluorophenyl —CH₃ Cl 3.43 366 2-chlorobenzyloxy —H 2-fluorophenyl —CH₃ Cl 3.21 367 3-chlorobenzyloxy —H 2-Fluorphenyl —CH₃ Cl 3.28 368 4-chlorobenzyloxy —H 2-fluorophenyl —CH₃ Cl 3.3 369 4-fluorobenzyloxy —H 2-Fluorphenyl —CH₃ Cl 2.98 370 —O—CH(CH₃)—CH₂—CH₃ —H 2-fluorophenyl —CH₃ Cl 2.87 371 3-trifluoromethylbenzyloxy —H 2-fluorophenyl —CH₃ Cl 3.38 372 -n-butoxy —H 2-fluorophenyl —CH₃ Cl 2.98 373 allyloxy —H 2-fluorophenyl —CH₃ Cl 2.42 374 t-butoxy —H 2-fluorophenyl —CH₃ Cl 2.75 375 2-hexahydropyranyloxy —H 2-fluorophenyl —CH₃ Cl 2.59 376 —O—CH₃ —H 2-fluorophenyl —CH₃ Cl 2.03 377 —O—CH₃ —CH₃ 2-fluorophenyl —CH₃ Cl 2.5 378 O-isopropyl —H 2-fluorophenyl —CH₃ Cl 2.54 379 1-cyclopropylethyl —H 2,4,6-trifluorophenyl —CH₃ Cl 3.09 380 —CH₂—CF₃ —C₂H₅ 2,4,6-trifluorophenyl —CH₃ Cl 3.42 381 —CH₃ —CH₃ 2-fluorophenyl —CH₃ Cl 2.34 382 —CH₂—CH(CH₃)—O—CH(CH₃)—CH₂— 2-fluorophenyl —CH₃ Cl 2.8 383 —C₂H₅ —H 2-fluorophenyl —CH₃ Cl 2.3 384 —CH₂—CH₂—CH₂—CH₂—CH₂— 2-fluorophenyl —CH₃ Cl 3.19 385 cyclopentyl —H 2-fluorophenyl —CH₃ Cl 3.11 386 -isopropyl —H 2-fluorophenyl —CH₃ Cl 2.63 387 —C₂H₅ —C₂H₅ 2-fluorophenyl —CH₃ Cl 2.95 388 —CH₂—CH₂—O—CH₂—CH₂— 2-fluorophenyl —CH₃ Cl 2.16 389 —CH₃ —H 2-fluorophenyl —CH₃ Cl 2.02 390 cyclopropyl —H 2-fluorophenyl —CH₃ Cl 2.41 391 —CH₂—CF₃ —H 2-fluorophenyl —CH₃ Cl 2.53 392 —CH₂—CH₂—CH(CF₃)—CH₂—CH₂— 2-fluorophenyl —CH₃ Cl 3.37 393 cyclopropylmethyl —H 2-fluorophenyl —CH₃ Cl 2.72 394 —CH₂—C(CH₃)═CH₂ —H 2-fluorophenyl —CH₃ Cl 2.68 395 —CH₂—CH₂—CF₃ —H 2-fluorophenyl —CH₃ Cl 2.7 396 1-cyclohexylethyl —H 2-fluorophenyl —CH₃ Cl 4.16 397 cyclohexyl —H 2-fluorophenyl —CH₃ Cl 3.43 398 2-trifluoromethylcyclohexyl —H 2-fluorophenyl —CH₃ Cl 3.49 399 3,5-bis-trifluoromethylcyclohexyl —H 2-fluorophenyl —CH₃ Cl 3.73 400 4-trifluoromethylcyclohexyl —H 2-fluorophenyl —CH₃ Cl 3.48 401 —CH₂—CH₂—CH₂—CH₂—CH(CH₃)— 2-chlorophenyl —CH₃ Cl 3.91 402 —CH₂—CH₂—CHF—CH₂—CH₂— 2-chlorophenyl —CH₃ Cl 3.05 403 —CH₂—CN —H 2-chlorophenyl —CH₃ Cl 2.03 404 (2-furyl)methyl —C₂H₅ 2-chlorophenyl —CH₃ Cl 3.56 405 cyclopentyl —H 2,4-difluorophenyl —CH₃ Cl 3.24 406 —CH₂—CF₃ —H 2,4-difluorophenyl —CH₃ Cl 2.68 407 —C(CH₃)₂—CH₂—COCH₃ —H 2,4-difluorophenyl —CH₃ Cl 2.53 408 2-trifluoromethylcyclohexyl —H 2,4-difluorophenyl —CH₃ Cl 3.56 409 4-trifluoromethylcyclohexyl —H 2,4-difluorophenyl —CH₃ Cl 3.56 410 —CH₂—COOC₂H₅ —CH₃ 2,4-difluorophenyl —CH₃ Cl 2.8 411 —CH₂—CH₂—CN —CH₃ 2,4-difluorophenyl —CH₃ Cl 2.34 412 —CH₂—CN —CH₃ 2,4-difluorophenyl —CH₃ Cl 2.34 413 —CH₂—CH₂—CN —C₂H₅ 2,4-difluorophenyl —CH₃ Cl 2.58 414 —CH₂—COOC₂H₅ cyclopropyl 2,4-difluorophenyl —CH₃ Cl 3.29 415 —CH₂—CH(OH)—CH₂—CH₂— 2,4-difluorophenyl —CH₃ Cl 1.95 416 2-methoxyethyl n-propyl 2-chlorophenyl —CH₃ Cl 3.36 417 —CH(CH₃)—CH═CH₂ —H 2,4,6-trifluorophenyl —CH₃ Cl 2.85 418 —CH₃ —CH₃ 2,6-difluorophenyl —CH₃ Cl 2.37 419 —C₂H₅ —H 2,6-difluorophenyl —CH₃ Cl 2.31 420 —CH₂—CN —H 2,6-difluorophenyl —CH₃ Cl 1.91 421 —C(CH₃)₂—CF₃ —H 2,6-difluorophenyl —CH₃ Cl 3.34 422 —CH₃ —H 2,6-difluorophenyl —CH₃ Cl 2.03 423 —CH(CF₃)—CH₂—CH₂—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 3.33 424 —CH₂—CF₃ —H 2,6-difluorophenyl —CH₃ Cl 2.56 425 2-trifluoromethylcyclohexyl —H 2,6-difluorophenyl —CH₃ Cl 3.52 426 —OH -isopropyl 2,6-difluorophenyl —CH₃ Cl 2.52 427 benzyloxy —H 2,6-difluorophenyl —CH₃ Cl 2.93 428 3,5-dichlorbenzyloxy —H 2,6-difluorophenyl —CH₃ Cl 3.75 429 2,4-dichlorbenzyloxy —H 2,6-difluorophenyl —CH₃ Cl 3.69 430 4-trifluoromethylbenzyloxy —H 2,6-difluorophenyl —CH₃ Cl 3.44 431 2-chlorobenzyloxy —H 2,6-difluorophenyl —CH₃ Cl 3.13 432 4-fluorobenzyloxy —H 2,6-difluorophenyl —CH₃ Cl 2.9 433 3-trifluoromethylbenzyloxy —H 2,6-difluorophenyl —CH₃ Cl 3.41 434 -n-butoxy —H 2,6-difluorophenyl —CH₃ Cl 2.96 435 2,6-dichlorbenzyloxy —H 2,6-difluorophenyl —CH₃ Cl 3.31 436 —O—CH₃ —H 2,6-difluorophenyl —CH₃ Cl 2.07 437 2,2,2-trifluoro-1-methylethyl —H 2-chlorophenyl —CH₃ Cl 3.1 438 2,2,2-trifluoro-1-methylethyl —H 2-chlorophenyl —CH₃ F 2.97 439 2-fluorocyclopropyl —H 2,4,6-trifluorophenyl —CH₃ Cl 2.3 440 —CH₂—COOC₂H₅ cyclopropyl 2,6-difluorophenyl —CH₃ Cl 3 441 —CH₂—CH(NH₂)—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 1.19 442 —CH₂—CH₂—CH(COCH₃)—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 2.49 443 —CH₂—CH₂—CHF—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 2.85 444 4-Tolyl —H 2,6-difluorophenyl —CH₃ Cl 3.01 445 4-fluorophenyl —H 2,6-difluorophenyl —CH₃ Cl 2.71 446 AB28 2,6-difluorophenyl —CH₃ Cl 3.34 447 —CH₂—C(CH₃)═CH₂ —C₂H₅ 2-chlorophenyl cyclopropyl Cl 4.59 448 —CH₂—C(CH₃)═CH₂ —C₂H₅ 2,4,6-trifluorophenyl cyclopropyl Cl 4.49 449 —CH₂—C(CH₃)═CH₂ —C₂H₅ 2-chloro-6-fluorophenyl cyclopropyl Cl 4.61 450 AB8 2,4-difluorophenyl —CH₃ Cl 1.73 451 —CH₂—CH(CH₃)—CH₂—CH(CH₃)—CH₂— 2,4-difluorophenyl —CH₃ Cl 4.16 452 —CH₂—CH(OH)—CH₂—CH₂—CH₂— 2,4-difluorophenyl —CH₃ Cl 2.2 453 —CH(COOCH₃)—CH₂—CH₂—CH₂—CH₂— 2,4-difluorophenyl —CH₃ Cl 3.36 454 —CH₂—CH₂—CHF—CH₂—CH₂— 2,4-difluorophenyl —CH₃ Cl 2.96 455 —CH₂—CH(CH₃)—O—CH(CH₃)—CH₂— 2,4-difluorophenyl —CH₃ Cl 2.94 456 3-tolyl —H 2,4-difluorophenyl —CH₃ Cl 3 457 2,2,2-trifluoro-1-methylethyl —H 2-chloro-6-fluorophenyl cyclopropyl Cl 3.59 458 2,2,2-trifluoro-1-methylethyl —H 2,4,6-trifluorophenyl cyclopropyl Cl 3.58 459 —NH—CH₂—CH₂—CH₂—CH₂— 2-chloro-6-fluorophenyl cyclopropyl Cl 3.46 460 isobutyl —H 2,4,6-trifluorophenyl cyclopropyl Cl 3.69 461 —CH₂—C(CH₃)₃ —H 2,4,6-trifluorophenyl cyclopropyl Cl 4.19 462 2-butyl —H 2,4,6-trifluorophenyl cyclopropyl Cl 3.69 463 cyclopentyl —H 2,4,6-trifluorophenyl cyclopropyl Cl 3.9 464 -isopropyl —H 2,4,6-trifluorophenyl cyclopropyl Cl 3.35 465 cyclopropylmethyl —H 2.4,6-trifluorophenyl cyclopropyl Cl 3.43 466 —CH₂—C(CH₃)═CH₂ —H 2,4,6-trifluorophenyl cyclopropyl Cl 3.34 467 isobutyl —CH₃ 2,4,6-trifluorophenyl cyclopropyl Cl 4.36 468 2-methoxyethyl —CH₃ 2,4,6-trifluorophenyl cydlopropyl Cl 3.29 469 —CH₂—C(CH₃)═CH₂ —CH₃ 2,4,6-trifluorophenyl cyclopropyl Cl 4.27 470 2-methoxyethyl —C₂H₅ 2,4,6-trifluorophenyl cyclopropyl Cl 3.64 471 —CH₂—CH₂—CH₂—CH(CH₃)— 2,4,6-trifluorophenyl cyclopropyl Cl 3.9 472 —CH₂—CH₂—CH₂—CH₂— 2,4,6-trifluorophenyl cyclopropyl Cl 3.52 473 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4,6-trifluorophenyl cyclopropyl Cl 4.66 474 —CH₂—CH₂—CH₂—CH₂—CH₂— 2,4,6-trifluorophenyl cyclopropyl Cl 4.22 475 —CH₂—CH₂—O—CH₂—CH₂— 2,4,6-trifluorophenyl cyclopropyl Cl 3.02 476 isobutyl —H 2-chloro-6-fluorophenyl cyclopropyl Cl 3.64 477 —CH₂—C(CH₃)₃ —H 2-chloro-6-fluorophenyl cyclopropyl Cl 4.08 478 2-butyl —H 2-chloro-6-fluorophenyl cyclopropyl Cl 3.66 479 cyclopentyl —H 2-chloro-6-fluorophenyl cyclopropyl Cl 3.83 480 -isopropyl —H 2-chloro-6-fluorophenyl cyclopropyl Cl 3 33 481 —CH₂—CF₃ —H 2-chloro-6-fluorophenyl cyclopropyl Cl 3.19 482 cyclopropylmethyl —H 2-chloro-6-fluorophenyl cyclopropyl Cl 3.4 483 —CH₂—C(CH₃)═CH₂ —H 2-chloro-6-fluorophenyl cyclopropyl Cl 3.31 484 —O—CH₂—CH₂—CH₂—CH₂— 2-chlorophenyl cyclopropyl Cl 3.71 485 —O—CH₂—CH₂—CH₂—CH₂— 2,4,6-trifluorophenyl cyclopropyl Cl 3.74 486 —O—CH₂—CH₂—CH₂—CH₂— 2-chloro-6-fluorophenyl cyclopropyl Cl 3.74 487 —NH—CH₂—CH₂—CH₂—CH₂— 2,4,6-trifluorophenyl cyclopropyl Cl 3.42 488 —NH—CH₂—CH₂—CH₂—CH₂— 2-chlorophenyl cyclopropyl Cl 3.39 489 2,2,2-trifluoro-1-methylethyl —H 2,4-difluorophenyl cyclopropyl Cl AS 3.51 490 2,2,2-trifluoro-1-methylethyl —H 2,4-difluorophenyl cyclopropyl Cl BS 3.52 491 —CH₂—C(CH₃)═CH₂ —C₂H₅ 2,4-difluorophenyl cyclopropyl Cl 4.37  96–98 492 isobutyl —H 2-chlorophenyl cyclopropyl Cl 3.76 493 —CH₂—CH₂—CH₂—CH₂—CH₂— 2-chlorophenyl cyclopropyl Cl 4.27 494 2-Butyl —H 2-chlorophenyl cyclopropyl Cl 3.76 495 —CH₂—C(CH₃)═CH₂ —H 2-chlorophenyl cyclopropyl Cl 3.41 496 —CH₂—C(CH₃)═CH₂ —CH₃ 2-chlorophenyl cyclopropyl Cl 4.32 497 isobutyl —CH₃ 2-chlorophenyl cyclopropyl Cl 4.41 498 —CH₂—CH₂—CH₂—CH(CH₃)— 2-chlorophenyl cyclopropyl Cl 3.99 499 —CH₂—CH₂—CH₂—CH₂—CH(CH₃)— 2-chlorophenyl cyclopropyl Cl 4.61 500 —CH₂—CF₃ —H 2-chlorophenyl cyclopropyl Cl 3.22 501 —CH(CF₃)—CH₂—CH₂—CH₂— 2-chlorophenyl cyclopropyl Cl 4.41 502 (2,2-dichlorocyclopropyl)methyl —CH₃ 2,4,6-trifluorophenyl —CH₃ Cl 3.68 503 -isopropyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl 3.5 504 —NH—CH₂—CH₂—CH₂—CH₂— 2-chloro-4-fluorophenyl cyclopropyl Cl 3.58 505 2,2,2-trifluoro-1-methylethyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl AS + BS 3.75 506 1,2-dimethylpropyl —H 2,4,6-trifluorophenyl —CH₃ Cl 3.35 507 (2,2-dichlorocyclopropyl)methyl —CH₃ 2,4-difluorophenyl cyclopropyl Cl 4.18 133–36 508 (2,2-dichlorocyclopropyl)methyl —CH₃ 2-chlorophenyl cyclopropyl Cl 4.29 509 (2,2-dichlorocyclopropyl)methyl —CH₃ 2,4,6-trifluorophenyl cyclopropyl Cl 4.26 510 (2,2-dichlorocyclopropyl)methyl —CH₃ 2-chloro-6-trifluorophenyl cyclopropyl Cl 4.37 511 —CH₂—CH═C(C₂H₅)—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 4.59 512 —CH₂—CH₂—CH═C(CH₃)—CH₂— 2,4-difluorophenyl cyclopropyl Cl 4.14 513 —CH₂—CH₂—CHF—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 3.45 514 AB12 2,4-difluorophenyl cyclopropyl Cl 3.78 515 —CH₂—CH₂—CH(CF₃)—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 4.07 516 —CH₂—CH₂—CH(NH—COCH₃)—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 2.2 517 —CH₂—CH₂—CH₂—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 4.03 518 —CH₂—CH₂—O—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 2.85 519 —CH₂—CH₂—S—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 3.58 520 AB14 2,4-difluorophenyl cyclopropyl Cl 4.25 521 4-tolyl —H 2,4-difluorophenyl cyclopropyl Cl 3.6 522 AB13 2,4-difluorophenyl cyclopropyl Cl 3.87 523 1,2-dimethylpropyl —H 2,4,6-trifluorophenyl —CH₃ Cl 3.38 524 —O—CH₂—CH₂—CH₂—CH₂— 2,6-difluorophenyl —CH₃ Cl 2.84 525 isobutyl —H 2,4-difluorophenyl —CF₃ Cl 4.03 526 n-butyl —H 2,4-difluorophenyl —CF₃ Cl 4.07 527 —CH₂—C(CH₃)₃ —H 2,4-difluorophenyl —CF₃ Cl 4.4 528 2-butyl —H 2,4-difluorophenyl —CF₃ Cl 4.03 529 —CH₂—CH₂—CF₃ —H 2,4-difluorophenyl —CF₃ Cl 3.7 530 cyclopentyl —H 2,4-difluorophenyl —CF₃ Cl 4.21 531 cyclopropyl —H 2,4-difluorophenyl —CF₃ Cl 3.49 532 —CH₂—CF₃ —H 2,4-difluorophenyl —CF₃ Cl 3.58 533 cyclopropylmethyl —H 2,4-difluorophenyl —CF₃ Cl 3.8 534 —CH₂—C(CH₃)═CH₂ —H 2,4-difluorophenyl —CF₃ Cl 3.75 535 t-butyl —H 2,4-difluorophenyl —CF₃ Cl 4.19 536 3-trifluoromethylcyclohexyl —H 2,4-difluorophenyl —CF₃ Cl 4.44 537 4-trifluoromethylcyclohexyl —H 2,4-difluorophenyl —CF₃ Cl 4.43 538 —CH₂—CH₂—N(CH₃)₂ —CH₃ 2,4-difluorophenyl —CF₃ Cl 1.77 539 propargyl —CH₃ 2,4-difluorophenyl —CF₃ Cl 3.65 540 1,3-dioxolan-2-ylmethyl —CH₃ 2,4-difluorophenyl —CF₃ Cl 3.62 541 allyl —CH₃ 2,4-difluorophenyl —CF₃ Cl 4.09 542 —CH₂—CH₂—CN —CH₃ 2,4-difluorophenyl —CF₃ Cl 3.19 543 (2-furyl)methyl —CH₃ 2,4-difluorophenyl —CF₃ Cl 4.11 544 isobutyl —CH₃ 2,4-difluorophenyl —CF₃ Cl 4.54 545 2-methoxyethyl —CH₃ 2,4-difluorophenyl —CF₃ Cl 3.73 546 —CH₂—C(CH₃)═CH₂ —CH₃ 2,4-difluorophenyl —CF₃ Cl 4.44 547 —CH₂—CH₂—N(CH₃)₂ —C₂H₅ 2,4-difluorophenyl —CF₃ Cl 1.91 548 allyl —C₂H₅ 2,4-difluorophenyl —CF₃ Cl 4.4 549 (2-furyl)methyl —C₂H₅ 2,4-difluorophenyl —CF₃ Cl 4.42 550 —CH₂—CH₂—CN —C₂H₅ 2,4-difluorophenyl —CF₃ Cl 3.46 551 —CH₂—COOC₂H₅ —C₂H₅ 2,4-difluorophenyl —CF₃ Cl 4.05 552 (2-tetrahydrofuryl)methyl n-propyl 2,4-difluorophenyl —CF₃ Cl 4.77 553 2-methoxyethyl n-propyl 2,4-difluorophenyl —CF₃ Cl 4.39 554 —CH₂—COOC₂H₅ cyclopropyl 2,4-difluorophenyl —CF₃ Cl 4.28 555 —CH₂—CH(OH)—CH₂—CH₂— 2,4-difluorophenyl —CF₃ Cl 2.76 556 cyclohexyl —H 2,4-difluorophenyl —CF₃ Cl 4.47 557 1-cyclohexylethyl —H 2,4-difluorophenyl —CF₃ Cl 5.12 558 2-methoxyethyl —C₂H₅ 2,4-difluorophenyl —CF₃ Cl 4.03 559 AB30 —H 2,4,6-trifluorophenyl —CH₃ Cl 3.71 560 n-butyl —H 2,6-difluorophenyl —CH₃ Cl 2.89 561 —CH₂—CH₂—N(CH₃)₂ —CH₃ 2,6-difluorophenyl —CH₃ Cl 1.28 562 —CH₂—COOC₂H₅ —CH₃ 2,6-difluorophenyl —CH₃ Cl 2.62 563 —CH₂—CH₂—CN —CH₃ 2,6-difluorophenyl —CH₃ Cl 2.17 564 —CH₂—CN —CH₃ 2,6-difluorophenyl —CH₃ Cl 2.18 565 —CH₂—COOCH₃ —CH₃ 2,6-difluorophenyl —CH₃ Cl 2.32 566 (2-furyl)methyl —CH₃ 2,6-difluorophenyl —CH₃ Cl 2.97 567 —CH₂—CH₂—N(CH₃)₂ —C₂H₅ 2,6-difluorophenyl —CH₃ Cl 1.46 568 allyl —C₂H₅ 2,6-difluorophenyl —CH₃ Cl 3.3 569 —CH₂—CH₂—CN —C₂H₅ 2,6-difluorophenyl —CH₃ Cl 2.41 570 2-thienylmethyl n-propyl 2,6-difluorophenyl —CH₃ Cl 3.96 571 —CH₂—CH₂—NH₂ -isopropyl 2,6-difluorophenyl —CH₃ Cl 1.28 572 AB31 2,6-difluorophenyl —CH₃ Cl 2.66 573 AB31 2,4,6-trifluorophenyl —CH₃ Cl 2.9 574 —O—CH₂—CH₂—CH₂—CH₂— 2,4,6-trifluorophenyl —CH₃ Cl 3.07 575 AB31 2,4-difluorophenyl —CH₃ Cl 2.74 576 —O—CH₂—CH₂—CH₂—CH₂— 2,4-difluorophenyl —CH₃ Cl 2.95 577 1,2-dimethylpropyl —H 2,4-difluorophenyl —CH₃ Cl 578 —CH(CH₃)—CH₂—CH₂—O— 2,6-difluorophenyl —CH₃ Cl 2.61 579 1,2-dimethylpropyl —H 2-chlorophenyl cyclopropyl Cl 4.14 580 —CH(CH₃)—CH═CH—CH(CH₃)— 2-chlorophenyl cyclopropyl Cl 4.19 581 1,2-dimethylpropyl —H 2,4,6-trifluorophenyl cyclopropyl Cl 4.03 582 —CH(CH₃)—CH═CH—CH(CH₃)— 2,4,6-trifluorophenyl cyclopropyl Cl 4.17 583 1,2-dimethylpropyl —H 2-chloro-6-fluorophenyl cyclopropyl Cl 4.12 584 —CH(CH₃)—CH═CH—CH(CH₃)— 2-chloro-6-fluorophenyl cyclopropyl Cl 4.15 585 —CH(CH₃)—CH₂—CH₂—O— 2,4,6-trifluorophenyl —CH₃ Cl 2.93 586 1,2-dimethylpropyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl AS + BR 4.25 587 1,2-dimethylpropyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl AR + BS 4.25 588 1,2-dimethylpropyl —H 2-chloro-4-fluorophenyl —CH₃ Cl 3.6 589 —O—CH₂—CH₂—CH₂—CH₂— 2-chloro-4-fluorophenyl —CH₃ Cl 3.23 590 AB31 2-chloro-4-fluorophenyl —CH₃ Cl 2.99 591 allyl —C₂H₅ 2,4-difluorophenyl cyclopropyl Cl 3.96 592 (2-furyl)methyl —C₂H₅ 2,4-difluorophenyl cyclopropyl Cl 3.97 593 (2-tetrahydrofuryl)methyl —C₂H₅ 2,4-difluorophenyl cyclopropyl Cl 3.78 594 2-Methoxyethyl —C₂H₅ 2,4-difluorophenyl cyclopropyl Cl 3.46 595 —CH₂—COOC₂H₅ —C₂H₅ 2,4-difluorophenyl cyclopropyl Cl 3.54 596 n-butyl —C₂H₅ 2,4-difluorophenyl cyclopropyl Cl 4.52 597 —C₂H₅ —C₂H₅ 2,4-difluorophenyl cyclopropyl Cl 3.73 598 cyclopropylmethyl n-propyl 2,4-difluorophenyl cyclopropyl Cl 4.53 599 (2-tetrahydropyranyl)methyl n-propyl 2,4-difluorophenyl cyclopropyl Cl 4.71 600 (2-tetrahydrofuryl)methyl n-propyl 2,4-difluorophenyl cyclopropyl Cl 4.22 601 2-thienylmethyl n-propyl 2,4-difluorophenyl cyclopropyl Cl 4.64 602 2-methoxyethyl n-propyl 2,4-difluorophenyl cyclopropyl Cl 3.84 603 —CH₂—CH(OH)—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 2.2 604 —CH₂—CH₂—CH₂—CH(CH₃)— 2,4-difluorophenyl cyclopropyl Cl 3.76 605 AB9 2,4-difluorophenyl cyclopropyl Cl 1.46 606 —CH₂—CH₂—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 3.36 607 —CH₂—CH₂—CH(OH)—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 2.29 608 —CH₂—CH₂—CH═CH—CH₂— 2,4-difluorophenyl cyclopropyl Cl 3.72 609 AB10 2,4-difluorophenyl cyclopropyl Cl 3.22 610 —CH₂—CH(CH₃)—CH₂—CH(CH₃)—CH₂— 2,4-difluorophenyl cyclopropyl Cl 4.72 611 —CH₂—CH₂—CH₂—CH₂—CH(CH₃)— 2,4-difluorophenyl cyclopropyl Cl 4.3 612 —CH₂—CH₂—CH₂—CH(CH₃)—CH₂— 2,4-difluorophenyl cyclopropyl Cl 4.37 613 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 4.41 614 —CH₂—CH(OH)—CH₂—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 2.57 615 —CH₂—CH₂—C(CH₃)₂—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 4.67 616 2-methoxyethyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl 3.07 617 —CH₂—CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-4-fluorophenyl cyclopropyl Cl 4.72 618 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-4-fluorophenyl cyclopropyl Cl 4.82 619 dimethylamino —H 2-chloro-4-fluorophenyl cyclopropyl Cl 3.29 620 1-cyclopropylethylamino —H 2-chloro-4-fluorophenyl cyclopropyl Cl 3.81 621 isobutyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl 3.9 622 —CH₂—C(CH₃)₃ —H 2-chloro-4-fluorophenyl cyclopropyl Cl 4.37 623 2-butyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl 3.9 624 cyclopentyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl 4.13 625 cyclopropylmethyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl 3.63 626 —CH₂—C(CH₃)═CH₂ —H 2-chloro-4-fluorophenyl cyclopropyl Cl 3.59 627 isobutyl —CH₃ 2-chloro-4-fluorophenyl cyclopropyl Cl 4.51 628 2-methoxyethyl —CH₃ 2-chloro-4-fluorophenyl cyclopropyl Cl 3.46 629 —CH₂—C(CH₃)═CH₂ —CH₃ 2-chloro-4-fluorophenyl cyclopropyl Cl 4.41 630 —CH₂—C(CH₃)═CH₂ —C₂H₅ 2-chloro-4-fluorophenyl cyclopropyl Cl 4.77 631 2-methoxyethyl —C₂H₅ 2-chloro-4-fluorophenyl cyclopropyl Cl 3.81 632 —C₂H₅ —C₂H₅ 2-chloro-4-fluorophenyl cyclopropyl Cl 4.13 633 —CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-4-fluorophenyl cyclopropyl Cl 4.08 634 —CH₂—CH₂—CH₂—CH₂— 2-chloro-4-fluorophenyl cyclopropyl Cl 3.72 635 —CH₂—CH₂—CH₂—CH₂—CH₂— 2-chloro-4-fluorophenyl cyclopropyl Cl 4.37 636 —CH₂—CH₂—O—CH₂—CH₂— 2-chloro-4-fluorophenyl cyclopropyl Cl 3.18 637 —CH(CH₃)—CH₂—CH(CH₃)₂ —H 2-chloro-4-fluorophenyl cyclopropyl Cl 4.61 638 —CH₂—CF₃ —H 2-chloro-4-fluorophenyl cyclopropyl Cl 3.37 639 —CH(CF₃)—CH₂—CH₂—CH₂— 2-chloro-4-fluorophenyl cyclopropyl Cl 4.23 640 2,2,2-trifluoro-1-methylethyl —H 2-chloro-4-fluorophenyl —CH₃ Cl AS + BS 3.19 641 2,2,2-trifluoro-1-methylethyl —H 2-chloro-4-fluorophenyl —CH₃ Cl AS 3.2 642 2,2,2-trifluoro-1-methylethyl —H 2-chloro-4-fluorophenyl —CH₃ Cl BS 3.17 643 —CH₂—C(CH₃)═CH₂ —C₂H₅ 2-chloro-4-fluorophenyl —CH₃ Cl 4.06 644 isobutyl —H 2,4-difluorophenyl cyclopropyl Cl 3.38 645 n-butyl —H 2,4-difluorophenyl cyclopropyl Cl 3.6 646 —CH₂—C(CH₃)₃ —H 2,4-difluorophenyl cyclopropyl Cl 4 647 2-butyl —H 2,4-difluorophenyl cyclopropyl Cl 3.57 648 —CH₂—CH₂—CF₃ —H 2,4-difluorophenyl cyclopropyl Cl 3.25 649 n-propyl —H 2,4-difluorophenyl cyclopropyl Cl 3.2 650 cyclopentyl —H 2,4-difluorophenyl cyclopropyl Cl 3.76 651 -isopropyl —H 2,4-difluorophenyl cyclopropyl Cl 3.2 652 cyclohexyl —H 2,4-difluorophenyl cyclopropyl Cl 4.02 653 1-cyclohexylethyl —H 2,4-difluorophenyl cyclopropyl Cl 4.84 654 2-methoxyethyl —H 2,4-difluorophenyl cyclopropyl Cl 2.75 655 cyclopropyl —H 2,4-difluorophenyl cyclopropyl Cl 2.95 656 cyclopropylmethyl —H 2,4-difluorophenyl cyclopropyl Cl 3.26 657 —CH₂—C(CH₃)═CH₂ —H 2,4-difluorophenyl cyclopropyl Cl 3.22 658 3-trifluoromethylcyclohexyl —H 2,4-difluorophenyl cyclopropyl Cl 3.98 659 4-trifluoromethylcyclohexyl —H 2,4-difluorophenyl cyclopropyl Cl 3.93 660 —CH(CH₃)—CH₂—CH(CH₃)₂ —H 2,4-difluorophenyl cyclopropyl Cl 4.24 661 —CH₂—CH₂—N(CH₃)₂ —CH₃ 2,4-difluorophenyl cyclopropyl Cl 1.56 662 propargyl —CH₃ 2,4-difluorophenyl cyclopropyl Cl 3.21 663 1,3-dioxolan-2-ylmethyl —CH₃ 2,4-difluorophenyl cyclopropyl Cl 3.1 664 allyl —CH₃ 2,4-difluorophenyl cyclopropyl Cl 3.61 665 3-(dimethylamino)-propyl —CH₃ 2,4-difluorophenyl cyclopropyl Cl 1.61 666 —CH₂—CH(OCH₃)₂ —CH₃ 2,4-difluorophenyl cyclopropyl Cl 3.24 667 (2-furyl)methyl —CH₃ 2,4-difluorophenyl cyclopropyl Cl 3.63 668 isobutyl —CH₃ 2,4-difluorophenyl cyclopropyl Cl 4.07 669 2-methoxyethyl —CH₃ 2,4-difluorophenyl cyclopropyl Cl 3.16 670 —CH₂—C(CH₃)═CH₂ —CH₃ 2,4-difluorophenyl cyclopropyl Cl 4.05 671 n-butyl —CH₃ 2,4-difluorophenyl cyclopropyl Cl 4.21 672 —CH₂—CF₃ —H 2,4,6-trifluorophenyl cyclopropyl Cl 3.25 673 —CH(CF₃)—CH₂—CH₂—CH₂— 2,4,6-trifluorophenyl cyclopropyl Cl 4.08 674 —CH₂—CH₂—CH₂—CH₂—CH(CH₃)— 2,4,6-trifluorophenyl cyclopropyl Cl 4.6 675 —CH₂—CH₂—CHF—CH₂—CH₂— 2,4,6-trifluorophenyl cyclopropyl Cl 3.68 676 isobutyl —CH₃ 2,6-difluorophenyl cyclopropyl Cl 4.08 677 —CH₂—C(CH₃)═CH₂ —CH₃ 2,6-difluorophenyl cyclopropyl Cl 3.98 678 —CH₂—CH₂—CH₂—CH(CH₃)— 2,6-difluorophenyl cyclopropyl Cl 3.68 679 —CH₂—CH₂—CH₂—CH₂— 2,6-difluorophenyl cyclopropyl Cl 3.25 680 —CH₂—CH₂—CH₂—CH₂—CH(CH₃)— 2,6-difluorophenyl cyclopropyl Cl 3.17 681 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,6-difluorophenyl cyclopropyl Cl 4.34 682 —CH₂—CH₂—CH₂—CH₂—CH₂— 2,6-difluorophenyl cyclopropyl Cl 3.9 683 —CH₂—CH₂—O—CH₂—CH₂— 2,6-difluorophenyl cyclopropyl Cl 2.78 684 1,2-dimethylpropyl —H 2,6-difluorophenyl —CH₃ Cl 3.18 685 —CH(CH₃)—C(CH₃)₃ —H 2,6-difluorophenyl —CH₃ Cl 3.56 686 —O—CH₂—CH₂—CH₂—CH(CH₃)— 2,4,6-trifluorophenyl —CH₃ Cl 3.42 687 —C₂H₅ —H 2,4-difluorophenyl —CH₃ Cl 3.08 688 1,2-dimethylpropyl —H 2-chloro-6-fluorophenyl —CH₃ Cl 3.43 689 AB31 2,4-difluorophenyl cyclopropyl Cl 3.32 690 —O—CH₂—CH₂—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 3.56 691 —NH—CH₂—CH₂—CH₂—CH₂— 2-chloro-4-fluorophenyl —CH₃ Cl 2.94 692 —NH—CH₂—CH₂—CH₂—CH₂— 2,4,6-trifluorophenyl —CH₃ Cl 2.83 693 —O—CH₂—CH₂—CH₂—CH(CH₃)— 2,4-trifluorophenyl —CH₃ Cl 3.3 694 —CH₂—CHF₂ —H 2,4,6-trifluorophenyl —CH₃ Cl 2 41 695 —CH(CH₃)—CH₂—CH₂—O— 2,4-difluorophenyl —CH₃ Cl 2.79 696 1,2-dimethylpropyl —H 2-chlorophenyl —CH₃ Cl 3.46 697 —CH₂—CHF₂ —H 2-chloro-4-fluorophenyl —CH₃ Cl 2.54 698 isobutyl —CH₃ 2-chloro-6-fluorophenyl cyclopropyl Cl 4.32 699 2-methoxyethyl —CH₃ 2-chloro-6-fluorophenyl cyclopropyl Cl 3.3 700 —CH₂—C(CH₃)═CH₂ —CH₃ 2-chloro-6-fluorophenyl cyclopropyl Cl 4.21 701 2-methoxyethyl —C₂H₅ 2-chloro-6-fluorophenyl cyclopropyl Cl 3.66 702 —CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-6-fluorophenyl cyclopropyl Cl 3.94 703 —CH(CF₃)—CH₂—CH₂—CH₂— 2-chloro-6-fluorophenyl cyclopropyl Cl 4.1 704 —CH₂—CH₂—CH₂—CH₂— 2-chloro-6-fluorophenyl cyclopropyl Cl 3.55 705 —CH₂—CH₂—CH₂—CH₂—CH(CH₃)— 2-chloro-6-fluorophenyl cyclopropyl Cl 4.54 706 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2-chloro-6-fluorophenyl cyclopropyl Cl 4.59 707 —CH₂—CH₂—CHF—CH₂—CH₂— 2-chloro-6-fluorophenyl cyclopropyl Cl 3.63 708 —CH₂—CH₂—CH₂—CH₂—CH₂— 2-chloro-6-fluorophenyl cyclopropyl Cl 4.19 709 —CH₂—CH₂—O—CH₂—CH₂— 2-chloro-6-fluorophenyl cyclopropyl Cl 3.05 710 2,2,2-trifluoro-1-methylethyl —H 2,4-dichlorophenyl cyclopropyl Cl AS 4.12 711 2,2,2-trifluoro-1-methylethyl —H 2,4-dichlorophenyl cyclopropyl Cl BS 4.19 712 —C₂H₅ —H 2,4-difluorophenyl cyclopropyl Cl 2.97 713 —CH₂—CN —H 2,4-difluorophenyl cyclopropyl Cl 2.42 714 —CH₂—CF₃ —H 2,4-difluorophenyl cyclopropyl Cl 3.17 715 2-trifluoromethylcyclohexyl —H 2,4-difluorophenyl cyclopropyl Cl 4.08 716 3,5-bis-trifluoromethylcyclohexyl —H 2,4-difluorophenyl cyclopropyl Cl 4.31 717 —CH₂—COOC₂H₅ —CH₃ 2,4-difluorophenyl cyclopropyl Cl 3.28 718 —CH₂—CH₂—CN —CH₃ 2,4-difluorophenyl cyclopropyl Cl 2.79 719 —CH₂—CN —CH₃ 2,4-difluorophenyl cyclopropyl Cl 2.79 720 —CH₂—COOCH₃ —CH₃ 2,4-difluorophenyl cyclopropyl Cl 2.95 721 —CH₂—CH₂—Cl —CH₃ 2,4-difluorophenyl cyclopropyl Cl 3.5 722 —CH₃ —CH₃ 2,4-difluorophenyl cyclopropyl Cl 3.06 723 —CH₂—CH₂—N(CH₃)₂ —C₂H₅ 2,4-difluorophenyl cyclopropyl Cl 1.65 724 —CH₂—CH₂—NH₂ —C₂H₅ 2,4-difluorophenyl cyclopropyl Cl 1.47 725 —CH₂—CH₂—CN —C₂H₅ 2,4-difluorophenyl cyclopropyl Cl 3.07 726 3-aminopropyl n-propyl 2,4-difluorophenyl cyclopropyl Cl 1.61 727 —CH₂—COOC₂H₅ cyclopropyl 2,4-difluorophenyl cyclopropyl Cl 3.84 728 AB8 2,4-difluorophenyl cyclopropyl Cl 2.17 729 —CH(CF₃)—CH₂—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 4.14 730 —CH₂—CH₂—CH(COCH₃)—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 3.07 731 —CH₂—CH₂—CH(COOCH₃)—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 3.38 732 —CH₂—CH₂—CHBr—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 4.08 733 —CH(COOCH₃)—CH₂—CH₂—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 3.92 734 AB11 2,4-difluorophenyl cyclopropyl Cl 1.55 735 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— 2,4-difluorophenyl cyclopropyl Cl 1.43 736 —CH₂—CH(CH₃)—O—CH(CH₃)—CH₂— 2,4-difluorophenyl cyclopropyl Cl 3.63 737 3-tolyl —H 2,4-difluorophenyl cyclopropyl Cl 3.61 738 4-fluorophenyl —H 2,4-difluorophenyl cyclopropyl Cl 3.27 739 -isopropyl —H 2,6-difluorophenyl cyclopropyl Cl 3.14 740 cyclopentyl —H 2,6-difluorophenyl cyclopropyl Cl 3.66 741 —CH₂—CHF₂ —H 2,4-dichlorophenyl cyclopropyl Cl 3.42 742 —CH₂—CF₃ —H 2,4-dichlorophenyl cyclopropyl Cl 3.72 743 AB31 2,6-difluorophenyl cyclopropyl Cl 3.23 744 isobutyl —H 2,6-difluorophenyl cyclopropyl Cl 3.44 745 (2,2-dichlorocyclopropyl)methyl —H 2-chlorophenyl cyclopropyl Cl 3.78 746 2,2,2-trifluoro-1-methylethyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl AS + BS + AR + BR 747 2,2,2-trifluoro-1-methylethyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl AS + BR 3.73 748 2,2,2-trifluoro-1-methylethyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl AR + AS 3.77 749 1,2-dimethylpropyl —H 2,4-dichlorophenyl cyclopropyl Cl 4.72 750 —NH₂ isobutyl 2,4-dichlorophenyl cyclopropyl Cl 4.36 751 1,2-dimethylpropyl —H 2,6-difluorophenyl cyclopropyl Cl 3.82 752 —CH₂—C(CH₃)═CH₂ —C₂H₅ 2,6-difluorophenyl cyclopropyl Cl 4.31 753 —O—CH₂—CH₂—CH₂—CH₂— 2,6-difluorophenyl cyclopropyl Cl 3.47 754 —NH₂ isobutyl 2,6-difluorophenyl cyclopropyl Cl 3.47 755 —NH—CH₂—CH₂—CH₂—CH₂— 2,4-dichlorophenyl cyclopropyl Cl 4.02 208–9 756 1,2-dimethylpropyl —H 2,4-dichlorophenyl cyclopropyl Cl AR 4.72 757 1,2-dimethylpropyl —H 2,4-dichlorophenyl cyclopropyl Cl BR 4.72 758 1,2-dimethylpropyl —H 2,4-dichlorophenyl cyclopropyl Cl AS 4.72 759 1,2-dimethylpropyl —H 2,4-dichlorophenyl cyclopropyl Cl BS 4.72 760 —CH₂—C(CH₃)═CH₂ —H 2,6-difluorophenyl cyclopropyl Cl 3.28 761 2-butyl —H 2,6-difluorophenyl cyclopropyl Cl 3.44 762 —CH₂—C(CH₃)₃ —H 2,6-difluorophenyl cyclopropyl Cl 3.9 763 —CH₂—CHF₂ —H 2,6-difluorophenyl cyclopropyl Cl 2.72 764 2,2,2-trifluoro-1-methylethyl —H 2,6-difluorophenyl cyclopropyl Cl 3.98 765 —CH(CH₃)—CH₂—CH₂—O— 2,6-difluorophenyl cyclopropyl Cl 3.26 766 —CH₂—CF₃ —H 2-chloro-4-fluorophenyl —CH₃ Cl 2.8 767 2,2,2-trifluoro-1-methylethyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl AS 3.73 768 2,2,2-trifluoro-1-methylethyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl BS 3.77 769 —CH₂—C(CH₃)═CH₂ —C₂H₅ 2,4-dichlorophenyl cyclopropyl Cl 5.25 770 AB32 2,6-difluorophenyl cyclopropyl Cl 3.32 771 —CH₂—CF₃ —H 2,6-difluorophenyl cyclopropyl Cl 3.04 772 —NH—CH₂—CH₂—CH₂—CH₂— 2,6-difluorophenyl cyclopropyl Cl 3.19 773 —NH₂ isobutyl 2,4,6-trifluorophenyl cyclopropyl Cl 3.65 186–8 774 AB33 —H 2,4-dichlorophenyl cyclopropyl Cl 2.7 775 1,2-dimethylpropyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl AR + BR 4.23 776 1,2-dimethylpropyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl BR 4.25 777 1,2-dimethylpropyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl AR 4.23 778 1,2-dimethylpropyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl AS 4.23 779 1,2-dimethylpropyl —H 2-chloro-4-fluorophenyl cyclopropyl Cl BS 4.23 780 AB31 2,4-dichlorophenyl —CH₃ Cl 3.41 781 2,2,2-trifluoro-1-methylethyl —H 2,4-dichlorophenyl —CH₃ Cl AS 3.55 210–1 782 2,2,2-trifluoro-1-methylethyl —H 2,4-dichlorophenyl —CH₃ Cl BS 3.58 216–7 783 —CH₂—C(CH₃)═CH₂ —C₂H₅ 2,4-dichlorophenyl —CH₃ Cl 4.56 784 —NH—CH₂—CH₂—CH₂—CH₂— 2,4-dichlorophenyl —CH₃ Cl 3.35 785 —O—CH₂—CH₂—CH₂—CH₂— 2-chloro-4-fluorophenyl cyclopropyl Cl 3.87 786 AB32 2,4,6-trifluorophenyl cyclopropyl Cl 3.56 787 1-methylethylideneamino isobutyl 2,6-difluorophenyl cyclopropyl Cl 4.21 788 1,2-dimethylpropyl —H 2,4-dichlorophenyl —CH₃ Cl 4.06 132–35 789 isobutyl —H 2,4-dichlorophenyl —CH₃ Cl 3.68 790 isobutyl —H 2,4-dichlorophenyl cyclopropyl Cl 4.3 791 —NH₂ isobutyl 2-chloro-6-fluorophenyl cyclopropyl Cl 3.74 175–6 792 —CH₂—CH₂—CH₂—CH(CH₃)— 2,4-difluorophenyl —CF₃ Cl 4.27 793 AB8 2,4-difluorophenyl —CF₃ Cl 2.56 794 —CH(CF₃)—CH₂—CH₂—CH₂— 2,4-difluorophenyl —CF₃ Cl 4.44 795 AB9 2,4-difluorophenyl —CF₃ Cl 1.67 796 AB10 2,4-difluorophenyl —CF₃ Cl 3.8 797 —CH₂—CH(CH₃)—CH₂—CH(CH₃)—CH₂— 2,4-difluorophenyl —CF₃ Cl 5.18 798 —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2,4-difluorophenyl —CF₃ Cl 4.8 799 —CH₂—CH(OH)—CH₂—CH₂—CH₂— 2,4-difluorophenyl —CF₃ Cl 3.07 800 —CH₂—CH₂—C(CH₃)₂—CH₂—CH₂— 2,4-difluorophenyl —CF₃ Cl 5.03 801 —CH₂—CH═C(C₂H₅)—CH₂—CH₂— 2,4-difluorophenyl —CF₃ Cl 4.95 802 —CH₂—CH₂—CH═C(CH₃)—CH₂— 2,4-difluorophenyl —CF₃ Cl 4.55 803 —CH₂—CH₂—CH(COOCH₃)—CH₂—CH₂— 2,4-difluorophenyl —CF₃ Cl 3.81 804 —CH(COOCH₃)—CH₂—CH₂—CH₂—CH₂— 2,4-difluorophenyl —CF₃ Cl 4.32 805 —CH₂—CH₂—CH(CF₃)—CH₂—CH₂— 2,4-difluorophenyl —CF₃ Cl 4.43 806 —CH₂—CH₂—CH(NH—COCH₃)—CH₂—CH₂— 2,4-difluorophenyl —CF₃ Cl 2.71 807 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— 2,4-difluorophenyl —CF₃ Cl 1.65 808 —CH₂—CH(CH₃)—O—CH(CH₃)—CH₂— 2,4-difluorophenyl —CF₃ Cl 4.1 809 —CH₂—CH₂—CH₂—CH₂—CH₂— 2,4-difluorophenyl —CF₃ Cl 4.45 810 —CH₂—CH₂—S—CH₂—CH₂— 2,4-difluorophenyl —CF₃ Cl 4.04 811 2-tolyl —H 2,4-difluorophenyl —CF₃ Cl 3.99 812 3-tolyl —H 2,4-difluorophenyl —CF₃ Cl 4.04 813 4-tolyl —H 2,4-difluorophenyl —CF₃ Cl 4.08 814 4-fluorophenyl —H 2,4-difluorophenyl —CF₃ Cl 3.69 815 AB13 2,4-difluorophenyl —CF₃ Cl 4.35 816 —NH₂ isobutyl 2,4-dichlorophenyl —CH₃ Cl 3.71 817 —O—CH₂—CH₂—CH₂—CH₂— 2,4-dichlorophenyl —CH₃ Cl 3.67 818 —CH(CH₃)—CH₂—CH(CH₃)₂ —H 2,4-difluorophenyl —CF₃ Cl 4.73 The logP values were determined in accordance with EEC directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile/0.1% aqueous phosphoric acid) *) Denotes that R¹ and R², together with the nitrogen atom to which they are attached, form a heterocyclic ring. **) The products were in some cases isolated as stereoisomers. “S” or “R” denotes S or R-configuration at the centre of chirality, respectively; “AS” denotes an unambiguous but unknown configuration at the centre of atropy and S configuration at the centre of chirality. BS denotes in each case the other, umambiguous but unknown configuration at the centre of atropy and S configuration at the centre of chirality. “AR” and “BR” in turn denote the respective complementary configurations at the centre of atropy coupled with the R configuration at the centre of chirality. Accordingly, in the case of identical substituents, “AR” and “BS”, and also “AS” and “BR”, are in each case pairs of enantiomers.

AB10

AB11

AB12

AB14

AB8

AB9

AB28

AB3

AB30

AB31

AB32

AB33

AB4

AB5

AB6

AB7

*marks in each case the bonding site Preparation of Starting Materials

Example 819

At room temperature, 2.6 g (7.43 mmol) of 2-trifluoromethyl-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine-5,7-diol are dissolved in 20 ml of phosphorus oxychloride, 1.2 g of phosphorus pentachloride are added a little at a time and the mixture is then heated under reflux for 6 hours. Volatile components of the reaction mixture are distilled off under reduced pressure. 20 ml of water are added to the residue and the mixture is extracted with 20 ml of dichloromethane. The organic phase is dried over sodium sulphate and chromatographed on silica gel using dichloromethane. This gives 1.2 g (37.6% of theory) of 5,7-dichloro-2-(trifluoromethyl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine.

HPLC: log P=3.71

Example 820

Process (e), first step:

1000 mg of ethyl N-methoxycarbamate are introduced in 10.0 ml of dimethylformamide and, in portions, 403 mg of sodium hydride are added, the temperature being adjusted to 30° C. by cooling. The reaction mixture is stirred at 30° C. for 2 hours and then 3500 mg of 2-bromoethyl methyl ether are added. The reaction mixture is stirred at 20° C. to 25° C. for 18 hours and then stirred into 20 ml of water. The reaction mixture obtained is concentrated to dryness under reduced pressure and extracted with four times 30 ml of dichloromethane. The organic extracts are dried over sodium sulphate, filtered and concentrated to dryness under reduced pressure.

This gives 1200 mg of ethyl (N-methoxy-N-methoxyethyl)carbamate (purity 77.6%, yield 62.6%).

Process (e), second stage:

200 mg of ethyl (N-methoxy-N-methoxyethyl)carbamate are introduced into 4.0 ml of aqueous ethanol (59%), 240.6 mg of potassium hydroxide are added and the mixture is stirred at 40° C. for 18 hours. The reaction mixture is then stirred into 50 ml of water and extracted with three times 20 ml of ethyl ether and with three times 20 ml of dichloromethane. The combined organic phases are washed with two times 20 ml of water, dried and concentrated to a volume of 20 ml at 20° C. under reduced pressure.

2 ml of hydrochloric acid are added to the resultant solution with ice cooling, after which the solution is stirred at room temperature for 1 hour and concentrated to dryness at 20° C. under reduced pressure.

The product obtained is digested with three times 15 ml of methanol and then concentrated to dryness at 20° C. under reduced pressure.

This gives 140 mg of N-methoxy-N-methoxyethylamine hydrochloride (yield 87.6%).

Example 821

Process (f), first stage:

A mixture of 1000 mg of ethyl N-hydroxy-N-methylcarbamate and 1166 mg of 2-bromoethyl methyl ether is heated to reflux temperature with stirring and then a solution of 493 mg of potassium hydroxide in 5 ml of ethanol is added dropwise. The reaction mixture is boiled under reflux for 10 hours and then worked up by filtering the reaction mixture and concentrating the filtrate under reduced pressure. The residue that remains is admixed with a mixture of water and ethyl acetate. The organic phase is separated off and washed first with saturated aqueous ammonium chloride solution and then with water. The organic phase is subsequently dried over sodium sulphate and concentrated under reduced pressure. This gives 0.7 g of a product which according to the gas chromatogram consists of 83% of ethyl (N-methyl-N-methoxyethoxy)carbamate. The yield is calculated accordingly to be 39% of theory.

Process (f), second stage:

A mixture of 200 mg of ethyl (N-methyl-N-methoxyethoxy)carbamate, 4 ml of ethanol and 4 ml of water is admixed with 240.6 mg of powdered potassium hydroxide and the mixture is stirred at 40° C. for 2 hours. The reaction mixture is subsequently stirred into 50 ml of water, then extracted with three times 20 ml of diethyl ether and subsequently with three times 20 ml of methylene chloride. The combined organic phase is washed with two times 20 ml of water, dried over sodium sulphate and concentrated to a volume of 20 ml at room temperature under reduced pressure. The solution obtained is admixed with 1 ml of ethereal hydrochloric acid, with ice cooling. The crystals which deposit are filtered off and dried. This gives 190 mg of N-methyl-N-methoxyethoxyamine hydrochloride.

Example 822

Process (g), first stage:

A mixture of 2000 mg of ethyl (2,2,2-trifluoro-1-methylethyl)carbamate and 20 ml of tetrahydrofuran is admixed at room temperature with 475 mg of sodium hydride, with stirring. Then a solution of 4600 mg of iodomethane in 10 ml of tetrahydrofuran is added dropwise at room temperature with stirring. The reaction mixture is stirred at 50° C. for 16 hours and then water is added. It is extracted with three times 20 ml of methylene chloride and the combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. This gives 1000 mg of a product which according to the gas chromatogram consists of 75% of ethyl N-(2,2,2-trifluoro-1-methylethyl)-N-methylcarbamate. The yield was calculated accordingly to be 34.86%.

Process (g), second stage:

A mixture of 1000 mg of ethyl N-(2,2,2-trifluoro-1-methylethyl)-N-methylcarbamate, 20 ml of ethanol and 20 ml of water is admixed with 1070 mg of powdered potassium hydroxide and the mixture is stirred at 40° C. for 66 hours. The reaction mixture is then diluted with water and extracted with three times 20 ml of a mixture consisting of equal parts of methylene chloride and diethyl ether. The combined organic phases are dried over sodium sulphate and then concentrated under slightly reduced pressure at room temperature. The solution obtained is admixed with ethereal hydrochloric acid, with ice cooling, and is stirred at room temperature for 60 hours. Concentration under reduced pressure gives 280 mg of N-(2,2,2-trifluoro-1-methylethyl)-N-methylamine hydrochloride. The yield was calculated accordingly to be 34% of theory.

Example 823

Process (h):

600 mg of benzyl N-(1-trifluoromethyl-2-propene)carbamate are heated under reflux in 8.0 ml of 16% strength hydrochloric, acid for 1.5 hours. After cooling to 20° C., the mixture is extracted with two times 20 ml of diethyl ether.

The aqueous phase which remains is concentrated to dryness under reduced pressure and admixed with three times 10 ml of methanol. After removal of the methanol under reduced pressure, 310 mg of (1-trifluoromethylprop-2-ene)amine hydrochloride are isolated. The yield is calculated accordingly to be 82.9% of theory.

The carbamate indicated in the tables below may also be prepared by the methods indicated above.

TABLE 2 (X)

Example No. Comp. No. R⁷ logP 824 X-2

2.38 825 X-3

2.06

TABLE 3 (XII)

Example No. Comp. No. R⁷ Physical constants 826 XII-2

TABLE 4 (XV)

Comp. Example No. No. R⁸ Physical constants 827 XV-2 —C₂H₅ ¹H-NMR (400 MHz, CD₃CN): δ (ppm) = 1.13(t, CH ₃CH₂N), 1.21(t, CH ₃CHCF₃), 1.23(t, CH ₃CH₂O), 3.20 (m, CH ₂N, CHCF₃), 4.1(q, CH₃ CH ₂O).

The amines set out in the table below may also be prepared by the methods indicated above.

TABLE 5 (III)

Example Comp. No. No. R¹ R² Physical constants 828 III-5

—OCH₃ ¹H-NMR (400 MHz, CD₃CN):δ (ppm) = 1.03(d, CH ₃)₂CH), 3.06(d, CH ₂), 3.28(b, (CH₃)₂ CH), 4.01(s, OCH₃) 829 III-6

—OCH₃ ¹H-NMR (400 MHz, DMSO):δ (ppm) = 1.76(s,CH ₃(CCH₂)CH₂), 3.29(b, NH,CH₃(CCH₂)CH ₂, OCH₃), 7.89,5.02(2s, CH₃(CCH ₂)CH₂). 830 III-7

831 III-8

—C₂H₅ ¹H-NMR (400 MHz, DMSO):δ (ppm) = 1.06(m, CH ₃CH₂N,CH ₃CHCF₃), 3.20(m, CH ₂N), 4.1(m, CHCF₃).

The amines set out in Examples 828 to 831 were each isolated and characterized in the form of their hydrochlorides.

Example 832

10.1 g (38.5 mmol) of dimethyl 2-(2,4,6-trifluoro-phenyl)malonate and 5.85 g (38.5 mmol) of 5-trifluoromethyl-1H-[1,2,4]triazol-3-ylamine in 10.1 ml of tri-n-butylamine are heated at 180° C. for 6 hours, during which the methanol that is formed is distilled off. The tri-n-butylamine is distilled off under strongly reduced pressure. This gives 17.8 g of crude 2-trifluoromethyl-6-(2,4,6-trifluoro-phenyl)-[1,2,4]triazolo[1,5-a]pyrimidine-5,7-diol which is reacted further without purification.

HPLC: log P=0.81

Example A

Puccinia Test (Wheat)/Protective

-   Solvent: 25 parts by weight of N,N-dimethylacetamide -   Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test for protective activity, the young plants are sprayed with the active compound preparation at the application rate indicated. After the spray coating has dried on, the plants are sprayed with a conidia suspension of Puccinia recondita. The plants spend 48 hours at 20° C. and 100% relative humidity in an incubation cabin.

The plants are then placed in a greenhouse at a temperature of about 20° C. and a relative humidity of 80% in order to promote the development of rust pustules.

Evaluation is made 10 days after inoculation. 0% denotes an efficacy corresponding to that of the control, while an efficacy of 100% denotes that no infestation is observed.

Active compounds, application rates and experimental results can be seen from the following table.

TABLE A Puccina test (wheat)/protective Application rate of active compound Active compound in g/ha Efficacy in % Inventive

(3) 500 100

Example B

Podosphaera Test (Apple)/Protective

-   Solvent: 24.5 parts by weight of acetone     -   24.5 parts by weight of dimethylacetamide -   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test for protective activity, the young plants are sprayed with the active compound preparation at the application rate indicated. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the apple mildew causative organism Podosphaera leucotricha. The plants are then placed in a greenhouse at about 23° C. and at a relative humidity of about 70%.

Evaluation is made 10 days after inoculation. 0% denotes an efficacy corresponding to that of the control, while an efficacy of 100% denotes that no infestation is observed.

Active compounds, application rates and experimental results can be seen from the following table.

TABLE B Podosphaera test (apple)/protective Application rate of active compound Active compound in g/ha Efficacy in % Inventive:

(7) 100 100

(8) 100 100

Example C

Spaerotheca Test (Cucumber)/Protective

-   Solvent: 49 parts by weight of N,N-dimethylformamide -   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test for protective activity, the young cucumber plants are sprayed with the active compound preparation at the application rate indicated. 1 day after treatment, the plants are inoculated with a spore suspension of Sphaerotheca fuliginea. The plants are then placed in a greenhouse at a temperature of 23° C. and at a relative humidity of 70%.

Evaluation is made 7 days after inoculation. 0% denotes an efficacy corresponding to that of the control, while an efficacy of 100% denotes that no infestation is observed.

Active compounds, application rates and experimental results can be seen from the following table.

TABLE C Spaerotheca test (cucumber)/protective Application rate of active compound Active compound in g/ha Efficacy in % Inventive:

(3) 750  93

(4) 750  93

(7) 750 100

(8) 750 100 

1. A triazolopyrimidine of formula (I)

in which R¹ represents amino, hydroxyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, optionally substituted cycloalkyloxy, optionally substituted alkylamino, optionally substituted dialkylamino, optionally substituted alkenylamino, optionally substituted alkynylamino, optionally substituted cycloalkylamino, optionally substituted N-cycloalkyl-N-alkylamino, optionally substituted alkylideneamino, optionally substituted phenyl, or optionally substituted heterocyclyl; or represents a radical of the formula —S—R⁵, in which R⁵ represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, or optionally substituted cycloalkyl, R² represents hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, or optionally substituted cycloalkyl, or R¹ and R² together with the nitrogen atom to which they are attached represent an optionally substituted heterocyclic ring, R³ represents optionally mono- to tetrasubstituted aryl, R⁴ represents optionally substituted cycloalkyl, and X represents halogen, with the proviso that if R¹ represents amino, then the compound of formula (I) is optionally an acid addition salt thereof.
 2. A triazolopyrimidine according to claim 1 in which R¹ represents hydroxyl or amino; represents alkyl having 1 to 6 carbon atoms that is optionally substituted by halogen, cyano, hydroxyl, amino, phenyl, heterocyclyl, alkoxy having 1 to 4 carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms, alkylamino having 1 to 4 carbon atoms, dialkylamino having 2 to 8 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, halogenocycloalkyl having 3 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 4 carbon atoms, oxo, hydroxyimino, and/or alkoxyimino having 1 to 4 carbon atoms; represents alkenyl having 2 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl, represents alkynyl having 2 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents cycloalkyl having 3 to 7 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, halogenoalkyl having 1 to 2 carbon atoms and 1 to 5 halogen atoms, phenyl, and/or heterocyclyl; represents alkoxy having 1 to 7 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents alkenyloxy having 2 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl, represents alkynyloxy having 2 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents cycloalkyloxy having 3 to 7 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents alkylamino having 1 to 7 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents dialkylamino having 1 to 7 carbon atoms in each of the alkyl radicals, each of which is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents alkenylamino having 2 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents alkynylamino having 2 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents optionally halogen-, cyano-, phenyl-, and/or heterocyclyl-substituted N-alkyl-N-alkenylamino having 1 to 6 carbon atoms in the alkyl moiety and 2 to 6 carbon atoms in the alkenyl moiety; represents cycloalkylamino having 3 to 7 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents N-cycloalkyl-N-alkylamino having 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 7 carbon atoms in the alkyl moiety and that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents alkylideneamino having 2 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents phenyl that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents heterocyclyl having 5 or 6 ring members that is optionally substituted by halogen, alkyl, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents heterocyclyloxy having 5 or 6 ring members that is optionally substituted by halogen, alkyl, cycloalkyl, cyano, phenyl, and/or heterocyclyl; or represents —SR⁵ in which R⁵ represents alkyl having 1 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents alkenyl having 2 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents alkynyl having 2 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl, or represents cycloalkyl having 3 to 7 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl, with the provisos that (1) each heterocyclyl radical is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, hydroxyl, phenyl, 1,2-dioxyethylene, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 halogen atoms, and halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 halogen atoms and each heterocyclyl radical is optionally saturated or partially unsaturated, and (2) each phenyl radical is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, and thiocarbamoyl; represents straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each having 1 to 6 carbon atoms; straight-chain or branched alkenyl or alkenyloxy, each having 2 to 6 carbon atoms; straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, or halogenoalkylsulphonyl, each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; straight-chain or branched halogenoalkenyl or halogenoalkenyloxy, each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl, or alkoximinoalkyl, each having 1 to 6 carbon atoms in the individual alkyl moieties; cycloalkyl having 3 to 6 carbon atoms; or is optionally substituted by 1,3-propanediyl, 1,4-butanediyl, methylenedioxy (—O—CH₂—O—), or 1,2-ethylenedioxy (—O—CH₂—CH₂—O—) attached in the 2,3-position, each of which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, and halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, R² represents hydrogen; represents alkyl having 1 to 4 carbon atoms that is optionally substituted by halogen, cycloalkyl having 3 to 6 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, oxo, hydroximino, and/or alkoximino having 1 to 4 carbon atoms; represents alkenyl having 2 to 4 carbon atoms that is optionally substituted by halogen and/or cycloalkyl having 3 to 6 carbon atoms; represents alkynyl having 2 to 4 carbon atoms that is optionally substituted by halogen, and/or cycloalkyl having 3 to 6 carbon atoms; or represents cycloalkyl having 3 to 6 carbon atoms that is optionally substituted by halogen and/or cycloalkyl having 3 to 6 carbon atoms, or R¹ and R², together with the nitrogen atom to which they are attached, represent a 3- to 6-membered heterocyclic ring that is saturated or partially saturated, that in addition to the nitrogen atom already mentioned optionally contain a further heteroatom selected from the series consisting of nitrogen, oxygen, and sulphur, and that is optionally substituted from one to three times by identical or different substituents selected from the group consisting of halogen, hydroxyl, cyano, morpholinyl, amino, a fused phenyl ring, a methylene or ethylene bridge, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms; alkylcarbonylamino having 1 to 4 carbon atoms, dialkylamino having 2 to 8 carbon atoms, alkoxycarbonylamino having 1 to 4 carbon atoms, di(alkoxycarbonyl)amino having 2 to 8 carbon atoms, hydroxyalkyl having 1 to 4 carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms, and alkylcarbonyl having 1 to 4 carbon atoms, R³ represents phenyl that is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl; straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl, or alkylsulphonyl, each having 1 to 6 carbon atoms; straight-chain or branched alkenyl or alkenyloxy, each having 2 to 6 carbon atoms; straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, or halogenoalkylsulphonyl, each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; straight-chain or branched halogenoalkenyl, or halogenoalkenyloxy, each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl, or alkoximinoalkyl, each having 1 to 6 carbon atoms in the individual alkyl moieties; and cycloalkyl having 3 to 6 carbon atoms; or is optionally substituted by 1,3-propanediyl, 1,4-butanediyl, methylenedioxy (—O—CH₂—O—), or 1,2-ethylenedioxy (—O—CH₂—CH₂—O—) attached in the 2,3-position, each of which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, and halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, R⁴ represents cycloalkyl having 3 to 6 carbon atoms that is optionally substituted by 1 to 9 halogen atoms, and X represents fluorine, chlorine, or bromine.
 3. A triazolopyrimidine according to claim 2 in which R¹ represents hydroxyl or amino; represents methyl, ethyl, n-propyl, isopropyl, n-, iso-, s-, or t-butyl, methoxymethyl, 2-methoxyethyl, methylthiomethyl, 2-methylthioethyl, hydroximinomethyl, methoximinomethyl, acetylmethyl, 2-hydroximinopropyl, 2-methoximinopropyl, allyl, 2-methylprop-2-enyl, propargyl, 2,2,2-trifluoroethyl, 1-(trifluoromethyl)ethyl, 3,3,3-trifluoropropyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, methylamino, ethylamino, n- or isopropylamino, n-, iso-, s-, or t-butylamino, dimethylamino, diethylamino, trifluoroethylamino, cyclohexylmethylamino, 2-cyanoethylamino, allylamino, 1-cyclopropylethylamino, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, 1-methylethylideneamino, phenyl, benzyloxy, piperidinyl, morpholinyl, pyridylmethoxy, or thiazolylmethoxy; represents —S—R⁵, in which R⁵ represents methyl, ethyl, n- or isopropyl, difluoromethyl, difluorochloromethyl, dichlorofluoromethyl, or trifluoromethyl; represents (2,2-dichlorocyclopropyl)methyl, (2-furyl)methyl, (2-tetrahydrofuryl)methyl, (2-tetrahydropyranyl)methyl, 1,2-dimethylpropyl, 1,3-dioxolan2-ylmethyl, 1-cyclopropylethyl, 1-cyclopropylethylamino, 1-methylethylideneamino, 2,2,2-trifluoro-1-methylethyl, 2,4-dichlorobenzyloxy, 2,6-dichlorobenzyloxy, 2-butyl, 2-chlorobenzyloxy, 2-fluorocyclopropyl, 2-hexahydropyranyloxy, 2-methoxyethyl, 2-thienylmethyl, 2-tolyl, 2-trifluoromethylcyclohexyl, 3-(dimethylamino)propyl, 3,5-bis-trifluoromethylcyclohexyl, 3,5-dichlorobenzyloxy, 3-aminopropyl, 3-chlorobenzyloxy, 3-tolyl, 3-trifluoromethylbenzyloxy, 3-trifluoromethylcyclohexyl, 2-trifluoromethylcyclohexyl, 4-trifluoromethylcyclohexyl, 4-chlorobenzyloxy, 4-fluorobenzyloxy, 4-fluorophenyl, 4-tolyl, 4-trifluoromethylbenzyloxy, 4-trifluoromethylcyclohexyl, allyloxy, —C(CH₃)₂—CF₃, —C(CH₃)₂—CH₂—COCH₃, —CH(CH₂OH)—COOCH₃, —CH(CH₃)—C(CH₃)₃—, —CH(CH₃)—CH(O—CH₃)₂—, —CH(CH₃)—CH═CH₂—, —CH(CH₃)—CH₂—CH(CH₃)₂—, —CH(CH₃)—CH₂—O—CH₃—, —CH(CH₃)—CH₂—OH, —CH(CH₃)—COOCH₃, —CH(CH₃)—COO—t-butyl, —CH₂—C(CH₃)═CH₂, —CH₂—C(CH₃)₃, —CH₂—CF₃, —CH₂—CH(OCH₃)₂, —CH₂—CH₂—CF₃, —CH₂—CH₂—Cl, —CH₂—CH₂—CN, —CH₂—CH₂—N(CH₃)₂, —CH₂—CH₂—N(CH₃)₂, —CH₂—CH₂—NH₂, —CH₂—CHF₂, —CH₂—CN, —CH₂—COOC₂H₅, —CH₂—COOC₂H₅, —CH₂—COOCH₃, cyclopropyl, cyclopropylmethyl, isobutoxy, isopropylamino, n-butoxy, —NH—CH₂—CF₂—CHF₂, —NH—CH₂—CF₃, —O—C₂H₅, —O—CH(CH₃)—CH₂—CH₃, —O—CH₃, O-isopropyl, propargyl, t-butoxy; or represents a group

wherein * represents the bonding site, wherein in each case the thiazolyl radical is optionally mono- or disubstituted and the pyridyl radical is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, n- or isopropyl, n-, iso-, s-, or t-butyl, methoxy, ethoxy, n- or isopropoxy, n-, iso-, s-, or t-butoxy, methylthio, ethylthio, n- or isopropylthio, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trifluoromethylthio, and phenyl, and wherein the phenyl and benzyloxy radicals are optionally substituted from one to three times in the phenyl moiety by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or isopropyl, n-, iso-, s-, or t-butyl, methoxy, ethoxy, n- or isopropoxy, methylthio, ethylthio, n- or isopropylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochioromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, tnfluoromethylsulphinyl, trifluoromethylsulphonyl, methylamino, ethylamino, n- or isopropylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl, or by 1,3-propanediyl, methylenedioxy (—O—CH₂—O—), or 1,2-ethylenedioxy (—O—CH₂—CH₂—O—) that are attached in the 2,3-position and are optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl and trifluoromethyl; R² represents hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, s-, or t-butyl, methoxymethyl, 2-methoxyethyl, methylthiomethyl, 2-methylthioethyl, hydroximinomethyl, methoximinomethyl, acetylmethyl, 2-hydroxyiminopropyl, 2-methoxyiminopropyl, allyl, propargyl, 2,2,2-trifluoroethyl, 1-(1,1,1-trifluoromethyl)ethyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, or cyclohexylmethyl, or R¹ and R², together with the nitrogen atom to which they are attached, represent 1-pyrrolinyl, 3-pyrrolinyl, pyrrolidinyl, dihydropyridinyl, piperidinyl, pyrazolinyl, pyrazolidinyl, imidazolinyl, imidazolidinyl, 1,2-diazinanyl, 1,3-diazinanyl, piperazinyl, oxazolinyl, oxazolidinyl, isoxazolyl, isoxazolidinyl, dihydrooxazinyl, morpholinyl, thiazolinyl, thiazolidinyl, or thiomorpholinyl, each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or isopropyl, n-, iso-, s-, or t-butyl, methoxy, ethoxy, n- or isopropoxy, methylthio, ethylthio, n- or isopropylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl, trifluoromethylsulphonyl, methylamino, ethylamino, n- or isopropylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, by a fused phenyl ring, or by a methanediyl or ethanediyl bridge; R³ represents phenyl that is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, formyl, methyl, ethyl, n- or isopropyl, n-, iso-, s-, or t-butyl, allyl, propargyl, methoxy, ethoxy, n- or isopropoxy, methylthio, ethylthio, n- or isopropylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, allyloxy, propargyloxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl, trifluoromethylsulphonyl, trichloroethinyloxy, trifluoroethinyloxy, chloroallyloxy, iodopropargyloxy, methylamino, ethylamino, n- or isopropylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl, or by 1,3-propanediyl, methylenedioxy (—O—CH₂—O—), or 1,2-ethylenedioxy (—O—CH₂—CH₂—O—) that is attached in the 2,3-position and are mono- or polysubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, and trifluoromethyl; R⁴ represents cyclopropyl; and X represents fluorine or chlorine.
 4. A triazolopyrimidine according to claim 2 in which R¹ and R² together represent —CH(CF₃)—CH₂—CH₂—CH₂—, —CH(CF₃)—CH₂—CH₂—CH₂—CH₂—, —CH(CH₃)—CH═CH—CH(CH₃)—, —CH(CH₃)—CH₂—CH₂—O—, —CH(COOCH₃)—, —CH₂—CH(CH₃)—CH₂—CH(CH₃)—CH₂—, —CH₂—CH(CH₃)—O—CH(CH₃)—CH₂—, —CH₂—CH(NH₂)—CH₂—CH₂— CH₂—C—CH₂—CH(OH)—CH₂—CH₂—, —CH₂—CH(OH)—CH₂—CH₂—CH₂— —CH₂—CH═C(C₂H₅)—CH₂—CH₂—, —CH₂—CH₂—C(CH₃)₂—CH₂—CH₂— —CH₂—CH₂—CH₂—, —CH₂—CH₂—CH(CF₃)—CH₂—CH₂— —CH₂—CH₂—CH(CH₃)—CH₂—CH₂—, —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— —CH₂—CH₂—CH(COCH₃)—CH₂—CH₂—, —CH₂—CH₂—CH(COOCH₃)—CH₂—CH₂— —CH₂—CH₂—CH(NH—COCH₃)—CH₂—CH₂—, —CH₂—CH₂—CH(OH)—CH₂—CH₂— —CH₂—CH₂—CH═C(CH₃)—CH₂—, —CH₂—CH₂—CH═CH—CH₂— —CH₂—CH₂—CH₂—CH(CH₃)—, —CH₂—CH₂—CH₂—CH(CH₃)—CH₂— —CH₂—CH₂—CH₂—CH₂—, —CH₂—CH₂—CH₂—CH₂—CH(CH₃)— —CH₂—CH₂—CH₂—CH₂—CH₂—, —CH₂—CH₂—CHBr—CH₂—CH₂— —CH₂—CH₂—CHF—CH₂—CH₂—, —CH₂—CH₂—N(CH₃)—CH₂—CH₂— —CH₂—CH₂—O—CH₂—CH₂—, —CH₂—CH₂—S—CH₂—CH₂— —CH₂—S—CH₂—CH₂—, —NH—CH₂—CH₂—CH₂—CH₂—, —O—CH₂—CH₂—CH₂—CH(CH₃)—, or —O—CH₂—CH₂—CH₂—CH₂—; or represent a group

wherein * represents the bonding site; R² represents hydrogen, methyl, ethyl, n-, isopropyl, or n-, iso-, s-, or t-butyl, R³ represents phenyl that is mono- to trisubstituted by identical or different fluorine and/or chlorine substituents in positions 2,4, and/or 6; and X represents chlorine.
 5. A triazolopyrimidine according to claim 2 in which R³ represents 2,4-disubstituted, 2,6-disubstituted, or 2,4,6-trisubstituted phenyl.
 6. A triazolopyrimidine according to claim 2 in which R³ represents 2-chloro-4-fluorophenyl, 2-chloro-6-fluorophenyl, or 2-chloro-4,6-difluorophenyl.
 7. A triazolopyrimidine according to claim 3 in which R³ represents 2,4-disubstituted, 2,6-disubstituted, or 2,4,6-trisubstituted phenyl.
 8. A triazolopyrimidine according to claim 3 in which R³ represents 2-chloro-4-fluorophenyl, 2-chloro-6-fluorophenyl, or 2-chloro-4,6-difluorophenyl.
 9. A triazolopyrimidine according to claim 2 in which R¹ represents hydrogen, and R² represents —CH(CH₃)CF₃.
 10. A triazolopyrimidine according to claim 3 in which R¹ represents hydrogen, and R² represents —CH(CH₃)CF₃.
 11. A triazolopyrimidine according to claim 2 in which R⁴ represents cyclopropyl.
 12. A triazolopyrimidine according to claim 3 in which R⁴ represents cyclopropyl.
 13. A dihalogeno-triazolopyrimidine of formula (II)

in which R³ represents optionally mono- to tetrasubstituted aryl, R⁴ represents optionally substituted alkyl or represents optionally substituted cycloalkyl, X represents halogen, and Y¹ represents halogen.
 14. A dihydroxy-triazolopyrimidine of formula (V)

in which R³ represents optionally mono- to tetrasubstituted aryl, and R⁴ represents optionally substituted alkyl or represents optionally substituted cycloalkyl.
 15. A composition for controlling unwanted microorganisms comprising (a) one or more triazolopyrimidines of formula (I)

or an acid addition salt thereof, in which R¹ represents amino, hydroxyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, optionally substituted cycloalkyloxy, optionally substituted alkylamino, optionally substituted dialkylamino, optionally substituted alkenylamino, optionally substituted alkynylamino, optionally substituted cycloalkylamino, optionally substituted N-cycloalkyl-N-alkylamino, optionally substituted alkylideneamino, optionally substituted phenyl, or optionally substituted heterocyclyl; or represents a radical of the formula —S—R⁵, in which R⁵ represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, or optionally substituted cycloalkyl, R² represents hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, or optionally substituted cycloalkyl, or R¹ and R² together with the nitrogen atom to which they are attached represent an optionally substituted heterocyclic ring, R³ represents optionally mono- to tetrasubstituted aryl, R⁴ represents optionally substituted alkyl or represents optionally substituted cycloalkyl, and X represents halogen, and (b) one or more extenders and/or surfactants.
 16. A composition according to claim 15 in which, for the triazolopyrimidines of formula (I), R¹ represents hydroxyl or amino; represents alkyl having 1 to 6 carbon atoms that is optionally substituted by halogen, cyano, hydroxyl, amino, phenyl, heterocyclyl, alkoxy having 1 to 4 carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms, alkylamino having 1 to 4 carbon atoms, dialkylamino having 2 to 8 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, halogenocycloalkyl having 3 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 4 carbon atoms, oxo, hydroxyimino, and/or alkoxyimino having 1 to 4 carbon atoms; represents alkenyl having 2 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl, represents alkynyl having 2 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents cycloalkyl having 3 to 7 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, halogenoalkyl having 1 to 2 carbon atoms and 1 to 5 halogen atoms, phenyl, and/or heterocyclyl; represents alkoxy having 1 to 7 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents alkenyloxy having 2 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl, represents alkynyloxy having 2 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents cycloalkyloxy having 3 to 7 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents alkylamino having 1 to 7 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents dialkylamino having 1 to 7 carbon atoms in each of the alkyl radicals, each of which is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents alkenylamino having 2 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents alkynylamino having 2 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents optionally halogen—, cyano—, phenyl—, and/or heterocyclyl-substituted N-alkyl-N-alkenylamino having 1 to 6 carbon atoms in the alkyl moiety and 2 to 6 carbon atoms in the alkenyl moiety; represents cycloalkylamino having 3 to 7 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents N-cycloalkyl-N-alkylamino having 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 7 carbon atoms in the alkyl moiety and that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents alkylideneamino having 2 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents phenyl that is optionally substituted by halogen, cycloalkyl, cyano, phenyl ,and/or heterocyclyl; represents heterocyclyl having 5 or 6 ring members that is optionally substituted by halogen, alkyl, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents heterocyclyloxy having 5 or 6 ring members that is optionally substituted by halogen, alkyl, cycloalkyl, cyano, phenyl, and/or heterocyclyl; or represents —SR⁵ in which R⁵ represents alkyl having 1 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents alkenyl having 2 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl; represents alkynyl having 2 to 6 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl, or represents cycloalkyl having 3 to 7 carbon atoms that is optionally substituted by halogen, cycloalkyl, cyano, phenyl, and/or heterocyclyl, with the provisos that (1) each heterocyclyl radical is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, hydroxyl, phenyl, 1,2-dioxyethylene, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 halogen atoms, and halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 halogen atoms and each heterocyclyl radical is optionally saturated or partially unsaturated, and (2) each phenyl radical is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, and thiocarbamoyl; represents straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each having 1 to 6 carbon atoms; straight-chain or branched alkenyl or alkenyloxy, each having 2 to 6 carbon atoms; straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, or halogenoalkylsulphonyl, each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; straight-chain or branched halogenoalkenyl or halogenoalkenyloxy, each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl, or alkoximinoalkyl, each having 1 to 6 carbon atoms in the individual alkyl moieties; cycloalkyl having 3 to 6 carbon atoms; or is optionally substituted by 1,3-propanediyl, 1,4-butanediyl, methylenedioxy (—O—CH₂—O—), or 1,2-ethylenedioxy (—O—CH₂—CH₂—O—) attached in the 2,3-position, each of which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, and halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, R² represents hydrogen; represents alkyl having 1 to 4 carbon atoms that is optionally substituted by halogen, cycloalkyl having 3 to 6 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, oxo, hydroximino, and/or alkoximino having 1 to 4 carbon atoms; represents alkenyl having 2 to 4 carbon atoms that is optionally substituted by halogen and/or cycloalkyl having 3 to 6 carbon atoms; represents alkynyl having 2 to 4 carbon atoms that is optionally substituted by halogen, and/or cycloalkyl having 3 to 6 carbon atoms; or represents cycloalkyl having 3 to 6 carbon atoms that is optionally substituted by halogen and/or cycloalkyl having 3 to 6 carbon atoms, or R¹ and R², together with the nitrogen atom to which they are attached, represent a 3- to 6-membered heterocyclic ring that is saturated or partially saturated, that in addition to the nitrogen atom already mentioned optionally contain a further heteroatom selected from the series consisting of nitrogen, oxygen, and sulphur, and that is optionally substituted from one to three times by identical or different substituents selected from the group consisting of halogen, hydroxyl, cyano, morpholinyl, amino, a fused phenyl ring, a methylene or ethylene bridge, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms; alkylcarbonylamino having 1 to 4 carbon atoms, dialkylamino having 2 to 8 carbon atoms, alkoxycarbonylamino having 1 to 4 carbon atoms, di(alkoxycarbonyl)amino having 2 to 8 carbon atoms, hydroxyalkyl having 1 to 4 carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms, and alkylcarbonyl having 1 to 4 carbon atoms, R³ represents phenyl that is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl; straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl, or alkylsulphonyl, each having 1 to 6 carbon atoms; straight-chain or branched alkenyl or alkenyloxy, each having 2 to 6 carbon atoms; straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, or halogenoalkylsulphonyl, each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; straight-chain or branched halogenoalkenyl, or halogenoalkenyloxy, each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl, or alkoximinoalkyl, each having 1 to 6 carbon atoms in the individual alkyl moieties; and cycloalkyl having 3 to 6 carbon atoms; or is optionally substituted by 1,3-propanediyl, 1,4-butanediyl, methylenedioxy (—O—CH₂—O—), or 1,2-ethylenedioxy (—O—CH₂—CH₂—O—) attached in the 2,3-position, each of which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, and halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, R4 represents alkyl having I to 4 carbon atoms that is optionally substituted by 1 to 9 halogen atoms or represents cycloalkyl having 3 to 6 carbon atoms that is optionally substituted by 1 to 9 halogen atoms, and X represents fluorine, chlorine, or bromine.
 17. A method of controlling unwanted microorganisms comprising applying an effective amount of one or more triazolopyrimidines of formula (I) according to claim 1 or an acid addition salt thereof to the unwanted microorganisms and/or their habitat.
 18. A method of controlling unwanted microorganisms comprising applying an effective amount of a composition according to claim 15 to the unwanted microorganisms and/or their habitat.
 19. A process for preparing a triazolopyrimidine of formula (I) according to claim 1 comprising (a) reacting a dihalogeno-triazolopyrimidine of formula (II)

in which R³, R⁴, and X have the meanings given for formula (I) in claim 1, and Y¹ represents halogen with an amine of formula (III)

in which R¹ and R² have the meanings given for formula (I) in claim 1, optionally in the presence of a diluent and optionally in the presence of an acid acceptor, or (b) reacting a triazolopyrimidine of formula (Ia)

in which R², R³, R⁴ and X have the meanings given for formula (I) in claim 1, with a sulphenyl halide of formula (IV) Y²—S—R⁵ (IV) in which R⁵ has the meanings given for formula (I) in claim 1, and Y² represents halogen, optionally in the presence of a diluent and optionally in the presence of an acid acceptor.
 20. A process for preparing an acid addition salt of a triazolopyrimidine of formula (I) according to claim 1 in which R¹ represents amino comprising adding an acid to the compound of formula (I) in which R¹ represents amino.
 21. A process for preparing dihalogeno-triazolopyrimidines of formula (II) according to claim 13 comprising (c) reacting a dihydroxy-triazolopyrimidine of formula (V)

in which R³ and R⁴ have the meanings given for formula (II) in claim 13, with a halogenating agent, optionally in the presence of a diluent.
 22. A process for preparing a dihydroxy-triazolopyrimidine of formula (V) according to claim 14 comprising (d) reacting an arylmalonic ester of formula (VI)

in which R³ has the meanings given for formula (V) in claim 14, and R⁶ represents alkyl having 1 to 4 carbon atoms, with an aminotriazole of formula (VII)

in which R⁴ has the meanings given for formula (V) in claim 14, optionally in the presence of a diluent and optionally in the presence of an acid binder.
 23. A process for preparing a composition for controlling unwanted microorganisms comprising mixing a triazolopyrimidine of formula (I) according to claim 15 with one or more extenders and/or surfactants. 